This series of posts on building a core wardrobe has proved incredibly popular – and now has its own dedicated Guide page here

I’m sure it’s useful to guys that are just starting out, trying to decide whether to get that versatile pair of brown loafers or a more exciting navy wholecut. 

But I also find men who’ve been buying clothes for years find it interesting – because chances are they haven’t filled all these useful holes in their collection. They’ve likely been tempted by the same wholecuts, or perhaps a snuff-suede polo boot, at some point. 

In this post we look at shoes, and smart shoes in particular. 

These capsule collections apply to most men, but obviously you don’t need the same clothes if you work in a casual office rather than a formal one. (Hence the split between our business-suits instalment and the casual-suits one.) 

So these are suggestions for someone that works in a fairly smart environment. Though of course, you can also adjust the numbers of each shoe depending on your circumstances. If you’re in a suit 3 or 4 days out of five, you’ll likely need two pairs of black oxfords, rather than one. 

I’m going to use Stefano Bemer’s ‘Essenziale’ collection as the illustrations for the post, as they helpfully went through this exact exercise, picking out the shoes customers find most useful. Details at the bottom of this post. 

Of course, this doesn’t mean these precise Bemer styles and lasts are the only ones recommended. 

 

 

1. The black cap-toe oxford

If you ever want to be appear particularly smart, you’ll need a black shoe, and a cap-toe oxford covers the most bases. 

An oxford is the smartest lacing style there is (see sliding scale of formality on shoes here) and black is the smartest colour. 

The cap-toe make-up then sits halfway between a whole cut – with nothing interrupting that expanse of leather – and something with a lot going on, like a wingtip brogue. As a result, the cap toe is just about OK with black tie, not flashy in any way, and perfect for any business suit. 

 

 

2. The dark-brown oxford

Although everyone in a smart office needs a black shoe, they might find they get most use out of a dark-brown one. I certainly always have. 

Being dark-brown rather than black means it will still work with most suits, yet also be a good partner for a whole range of separate jackets and trousers. 

The one pictured is also a half-brogue (so still a lot of broguing/holes, but not as much as a wingtip shoe) which makes it a little more casual and differentiates it from the black shoe in another small way. 

 

 

3. The brown-suede loafer

There is an argument that this is the most versatile shoe on the whole list. 

A brown-suede loafer will be too casual for most business suits, but it’s great with casual suits. It will work with almost every separate jacket and trouser combination. With chinos and a shirt, and even some dark denim. 

Don’t wear it with your navy worsted two-piece, with the white shirt and tie. They’re just not smart enough. But they’re the shoe to have as a back-up, in the drawer of the desk, as they’ll be good for everything else. 

 

 

4. The black loafer

I’d push for two loafers in the top five. Because although a loafer is more casual than an oxford or even a slim derby, most colleagues will never think a black loafer is inappropriate with even the smartest suit. Colour and texture are much more important than style. 

So if you wear a lot of suits, I’d suggest your second black pair of shoes should be loafers. They’ll look more at home with smart trousers and a white shirt too. 

If you don’t wear smart suits that much, make this a pair of dark-brown leather loafers instead. 

 

 

5. The brown-suede chukka boot

This is not a smart-office shoe, except for those that still have a dress-down Friday or equivalent. It is not intended for suits. 

But with a pair of flannels and tweed jacket, it’s perfect. And it can be worn with pretty much everything at the weekend too. Especially good with jeans and an oxford shirt. 

Brown suede is the best colour, even if you have brown-suede blousons or other jackets. The brown is just really useful. The second pair can be tan or dark olive. 

 

 

Once you have an equivalent of that top five that works for your lifestyle, and only then, I’d suggest looking at more adventurous styles and colours – such as tan leather or monk straps (above). 

Unusual shoes are very attractive, but it’s much easier to wear the same shoes regularly than it is to wear the same jacket every day. I also personally find it more interesting to play with colours of tailoring like that, rather than shoes. 

The next five shoes in Bemer’s Essenziale collection show this move towards becoming more adventurous. They are:

  • Dark-brown suede derby
  • Black wingtip brogue
  • Tan derby (below)
  • Dark-brown monk strap (above)
  • Brown grain-leather derby (below, bottom)

 

 

The Essenziale collection is a set of Bemer shoes aimed at buying materials and making in bulk, to reduce prices and make those core styles more accessible. 

As a result the shoes cost €850 rather than the normal €1250, but are made to exactly the same standard. More details here.

They will be on show during the PS Presents pop-up shop in September, on Savile Row. Details here

 

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Matthew

I’m surprised more people don’t wear (and love) elastic sided shoes; they are as convenient as loafers to slip on and as smart as Oxfords in appearance, esp. if one has them with dummy laces. I am thoroughly addicted to them. GJ Cleverley or G&G are the obvious choices for this style, I think.

Also, I’m surprised more people don’t wear oxblood shoes. It is a surprisingly versatile colour, more so in my view than black or even brown.

Ian A

I see those shoes in Foster’s a lot when I indulgently take a stroll along London’s Jermyn Street!

Tom

A bad advise in my opinion, Ian. I buy Alden Cordovan since more than 20 years and with minimum care (shoe-tree, 2-3 days rest after use, regular polish w/o shoe cream) all of them are still in use, showing some patina, but all in perfect shape. The one and only exception was a pair of Penny-loafers! The construction of loafers in general allows too much flection of the sole, leading to wrinkles in the vamp as well as to an excessive separation between foot and the leather in the area above the heel.
As there is no significant price gap between the loafers and the lace-up’s, with a lifetime of less than 1/10th, the loafer is in my opinion definitely not worth the money.
After this experience my loafers are always much cheaper models w/o cordovan e.g. made by Allen Edmonds, which “survive” the same two seasons but save some 2/3rds oft the price of an Alden or any similar cordovan model.

AJ

Interesting list. It might just be the type of black loafer that tend to be worn, where the leather is cheap but I always think that black loafers look terrible – the style and colour just don’t seem to work together.

Evan Everhart

Try Alden. Their full strap penny loafer is exceptional. Even in black, better yet in black shell Cordovan (horsehide).

John

Simon, no brogues? You include them in the next 5 to get, but surely they deserve to be in everyday circulation? I am big fan of brogues as the detailing adds some interest; this is important given the dark colours that shoes often are. Love these capsule pieces, thanks!

Carl

I am also a bit skeptical about black loafers. But its probably because of the image of overweight midwestern Republican congressmen with bulky sport coats or suit jackets wearing black loafers in cheap (or fake) leather. I would probably replace the black loafers with brown brogues, perhaps country brouges with a rubber or double leather sole.

But I really like this articles.

Eugene

I’m surprised by the black loafer. It’s neither fish nor fowl. Black is formal, but loafer is informal. I’m equally surprised that there’s nothing in oxblood in the top 5, or even the second group. That seems a versatile color especially well matched with a navy suit, which is most common.

Anonymous

What shoes besides the black loafer do you wear or recommend most for knitwear + trousers? Would dark brown captoes work best?

Anonymous

Wouldn’t loafers, even the best bespoke ones, widen over time and become looser over time, especially if you have a slim heel? Can your shoemaker retighten the shoe after some wear?

Anonymous

I can note the shoe formality guide but don’t understand why a brown oxford would be too smart for knitwear + trousers?

JDV

In a formal environment I’d argue for a black perforated captoe as number 4. Still quite formal and yet wearable with flannel. (Something like STC 529SPE or maybe 645) And maybe an oxford boot rather than a chukka boot. Certainly more formal, even though not as versatile.

In an more casual environment I’d get these 5:
1. Brown-suede loafer (Preferably EG Piccadilly)
2. Dark brown oxford (Preferably STC 645)
3. Brown-suede oxford
4. Brown-suede chukka
5. Dark brown calf split toe derby by STC, Mod 575 (I dislike the EG dover)

Although I have around 20 pairs of shoes, (including your capsule collection) these get the most wear.

Chris

Hi Simon- i’m on a low to average income I guess for london and have started to buy better shoes, as an avid follower of your blog.
However, when I know what % of my income they involve, honestly it’s hard to wear them out. I find myself deeply protective of say wearing my Crockett and jones cavendish to a garden party, when they could be scuffed and muddy.
I’m curious to what extent you truest believe high quality shoes can last through the punishment of a garden party, a surprise rain storm, a bike ride you weren’t expecting with your child. or an unexpected muddy and stoney path for example . Am I right to be deeply protective or should I embrace it, and learn to deal with the shoe maintenance that follows? I would be very curious to hear your thoughts.

Malcolm

Dainite soles are a wise investment for occasions where the weather or underfoot surface is uncertain. I have a couple of pairs and find that can even do short distance bike rides wearing them.

Scott

This is a very helpful piece Simon. Personally I’m a big fan of black shoes and believe they are way underrated so, was I glad to see two of the top five in black. Of course I wear brown shoes more often as they are more versatile. The Bemer collection of core shoes is superb.

jamiemcp

I would possibly exclude the black loafer and replace it with either another pair of black or brown oxfords or even potential a pair of brown suede oxfords (this would be my choice, but it might be to casual for some)

I find a black loaf sits in a funny place, it’s neither formal nor informal

Evan Everhart

To me, black loafers are for once you already have all of yr other basics seen to and want something unusual for once in a while wear. I got a pair a while back, Alden full strap penny loafers and they are interesting with very casual black tie, or as an item to spruce up a navy or black and white Glen Urquhart check sport coat. They are a late addition shoe. Much like spectators or Scotch grain shoes, something to add to an already full stable of shoes, at least in my opinion.

The odd positioning of the black loafer with regards to its formality, is both its greatest asset and limitation, its neither one, nor the other, fish nor fowl.

Evan Everhart

Hi Simon,

I’d have chosen some different ones, just for versatility….

I find that I never wear my plain cap toe Balmoral laced Black Oxfords as I find them too unutterably boring with no real depth in the color, so I prefer my semi brogued black Church’s Diplomats (old, not new production – which aren’t as good), with the medallion on the toe. I would never wear black wingtips of any sort as they seem to me to be a sartorial mixed message, a confusion, even oxymoronic, in the most formal color with the most casual model of Oxford shoe….

Next down would be darkest brown Diplomat model shoes (I’m still hunting for a suitable pair but considering the Carmina model as the pair that I really want cost as much as a used car over at the Armoury).

Burgundy or real Cordovan pair of wingtips, are a basic every day shoe that can and does go with nearly everything but burgundy or red hosiery without being loud. and gives a nice variety to wear. Balmoral laced wingtips are the quintessential every day shoe and can be easily dressed up or down from a navy worsted suit down to a brown Shetland or Harris tweed suit or sportcoat, or even a gray or green model. I also recommend these in either deep mahogany brown or in a Scotch grain in tan for variety once basics have been acquired.

I’d say that after that, a pair of dark brown box calf or chestnut suede tassel loafers as made by Alden with their tastefully low vamp and instep would be a good shoe as it does go with everything, I’d go for the box calf, as I am generally against suede as its a bit fussy in foul weather and can be more difficult to maintain in areas that are not particularly clean or dry. The brown leather can be worn with any color of sock and is tastefully discrete.

As a final shoe, I would say that plain Cordovan Alden full strap penny loafers would be a go to shoe. They are for me, and this Friday, as most others, I am wearing them as they are comfortable, I can slip them off under my desk, and slip them on just as easily, and they always look discretely tasteful. They, also much like the tassel loafers can be worn with most anything that is not wine colored hosiery.

Just my two cents.

Simon, I really enjoyed this article! Thank you for posting it! It made me think about this, and I hadn’t in a very long time, not since I closed down my image consultation business.

Michael

Seeing these makes me feel I may be in a shoe rut – I tend to rotate through 5 pairs of Black cap-toe oxfords

Jan Willem

Many thanks for another great post, Simon. I personally really like the navy suit and dark brown suede loafers combo though! Perhaps not with the plainest worsted navy but definitely with a fresco or flannel or something else with some texture or pattern. And better without a tie. Second comment; I never understood derbies! Doesn’t appeal to me at all and would never buy a pair – funny how that works. Keep up the good work please

Anonymous

Simon, the link to the page containing more information about this line of Bemer’s shoes is not working. Just thought you should know.

Zo

good list, thank you for this. i work in the City of London and I find black oxford so incredibly ubiquitous here that I just cannot get my self to wear them. I almost exclusively wear loafers and monk straps, brown and black, and I find they work very well with all my suits and separates. And yes I 100% agree, the dark brown suede is the most versatile in the list…but perhaps not for rainy London!

David G

A bit of an over simplification really, but not a bad start.

Black lace-ups. Minimal or no brogue. With or without toe-cap.
Brown lace-ups, as above, toe cap or not.
Brown suede loafers. This is where it gets harder. Snuff? Mid? Espresso? Tassels?
Suede chukka; colour questions as above.
Black loafers; less formal than oxfords, but question tassels or not.

More to it than this simple start point…………………….

Ben

Hi Simon, I greatly enjoy your writing.

I’m hoping I can trouble you for your opinion. I am going to purchase a new pair of loafers. My question has to do with formality and congruence. It is also related to some of the comments above, especially the thoughts on black loafers.

I am looking at 2 models from Alden.
https://www.brogueshop.com/collections/alden/products/alden-hayvey-tassel-moccasin
https://www.brogueshop.com/collections/alden/products/alden-x-brogue-lounger-slip-on

For context, today I am wearing Anglo-Italian shaved cotton chinos, white linen shirt with the sleeves rolled up, no-show socks, and camp mocs in bison leather. Next week will see me in same AI or Drake’s chinos, Anglo-Italian sportjacket, Drake’s striped or denim or oxford shirt, and maybe a tie but most likely not.

I know the tassels work with the above. The lighter color, the “details” (tassels, stitching), make for a clearly casual, congruent and appropriate look. But how do you feel about the darker brown loafer? The color is darker, the design simpler, the last (slightly) more shapely (esp. the toe)…

Feurich

The brown suede tassel loafer is my total go to shoe. I find them more comfortable than lace ups, I can slip them off easily at my desk for some freedom, and they seem to go with everything, from suits to jeans. I also wear them with blue suits. I think they go fine. The problem is finding the ideal pair!

Sam Tucker

I’m a bit surprised that the black loafer is so hated. I’d have put it first in the list, especially for people that don’t dress up as much. It sits nicely between casual and formal, and goes equally well with a suit or with chinos. An alternative to the black loafer is a plain toe elastic on instep shoe. Edward Green unfortunately only has them in suede at the moment, but C&J has a black calf leather one in their 2019 AW catalog. The thing I love about such a shoe is it can be seen either as a highly formal plain-toe gusset black shoe, or as a more casual demi-boot.

Ben

After the cap-toes there’s really no essential shoe, so any choice of five would be controversial.

I’m in some snowy winters and rely on boots quite a bit. Chelseas and wingtips over chukkas always. Suede loafers have no chance in such a climate.

Sam Tucker

I’m glad you put a black shoe first. Blacks shoes are much too denigrated as boring or as clashing with trousers. Black calf leather shoes have a bright shine and smart look when polished that no other colour can match. There are very few other things so shiny a man can wear without looking flashy and pushing the limits of taste. The only colours black clashes with are very dark ones like navy, anything else it has a nice contrast against, including tobacco brown (Simon’s tobacco suit looked very, very nice against his black knit tie) and mid or lighter blue. But because the texture of calf leather is so different from suiting and trousering, colours that would normally clash with black like navy look fine together when wearing black shoes with navy suits.

Scott

No doubt that black shoes are under appreciated. A black suede lace up split toe, loafer, and Chelsea boot are all fantastic and provide a very sophisticated look.

Anonymous

Black toe-cap, black brogue, brown adelaide, brown suede brogue, brown plain toe.
Oxblood and tan, split toe, norwegian, whole cut, monk strap, country weight (Loake) etc. offer further options.
A chukka boot is a boot so shouldn’t really be in the list but I’d add a chelsea or oxford laced boot as boot options. As with Evan I’d pick loafers last as they come after a proper, laced shoe collection, they are also less wearable in winter (due to weight and construction).

Max

Very interesting article Simon.

I’ve got variations of all the shoes you mention, but I find that I am still lacking one thing which is shoes for very rainy days. Currently my only real options are an old pair of Meermin boots and some C&J suede chukkas. I know others have commented they wouldn’t wear suede in the rain but I much prefer that to ruining some E&G cordovans!

I’m curious to hear what you would wear as you certainly get a good downpour every once in a while in London.

Sam

Living in Amsterdam and cycling about an hour a day, my shoes get a fair bit of rain. I often wear shell cordovan, and unfortunately I find it very fussy with water, more than calf. I’ve tried waxes and Alden’s Leather Defender spray, but whatever I do, I get white spots with a single drop of rain. Suede has a reputation of being vulnerable, but I actually find it to hold up much better than calf or shell, with only minimal maintenance required.

Alex

Hi Simon, thanks for the useful info. could you please let me know what cream you are referring to here? Is it the colour 8 paste from Alden or is there something else that I need to get rid of rain stains? Thank you in advance.

Alex

Oh and what are your view on the Alden leather defender? Thinking of getting one but thought I’d check with you first. Thanks!

E L

Thought I might chime in as I walk in pouring rain for extended periods of time quite frequently. Rubber soles, e.g. dainite, are nice. Even better if you can get a thicker rubber sole, e.g. a double dainite sole (not sure if that is really a thing, but some of my dainite soles are significantly thicker than others). This gives the shoe more elevation which helps with puddles and such. I believe water getting into the area where the sole meets the upper can lead to wet feet. Thicker soles prevent this.

I don’t have experience with Cordovan. Suede is fine. As Simon pointed out, you do have to brush it out afterwards though. Also, I find that if I am in a lot of rain, my feet will still get quite wet with suede, which isn’t very pleasant if you have to stay in your shoes after you are outside in the rain.

I think a pebble/scotch-grain (is there a difference?) is The Best, especially the grains that are more textured. For starters, I think the scotch-grain texture makes it harder for water to sit on the surface. More importantly, though, is that scotch-grain really eats up shoe creams and polishes (if you have grain shoes you know what I am talking about). Shoe creams and polishes contain fats (often wax) which are hydrophobic and thus water repellent. Accordingly, if you have a good amount of buildup on the shoe (the creases are hardest to get) the water should run right off and your shoe should still look pretty dry and need no maintenance (aside from trees) after walking in the rain.

Some shoe styles are also better for the rain. Boots are good. NSTs and PTBs are also pretty good in my experience. Brogueing leads to wet feet.

Alex N.

Dear Simon,
For the brown suede loafer what style would you recommend if one finds the tassel loafer too effeminate ? Would a penny still work in suede?
Best Regards,
Alex

Kirill

Hi Simon,

Thanks for the article, really useful.

May I trouble you with an unrelated question though. I had sent a week or two ago the email to the permanent style shop support address about the delivery to Russia; basically, I’ve asked if the shop delivers to Russia, and if yes, which courier company is used. Unfortunately, I have not received a reply. Would appreciate any comments. Thanks in advance.

Anonymous

Worth mentioning that whilst the list is a great start for the consideration of a shoe collection fit is most important of all. I mention this as Jan points to derbies – for those with a high arch or wide feet oxfords, unless bespoke or a G+ width, are often too narrow (the average European/UK width is F), derbies therefore give a latitude of extra comfort. Chukkas, as they have a derby lacing are also comfortable for this reason. As with oxfords loafers can present similar width and fit problems and, especially if there is ‘beef roll’ side stitching, stretching through wear will be negligible.

John

Hi Simon,
I wish I had the opportunity to read such a rationale for buying a pair of black loafers at the time I bought my second pair of black oxfords instead, even though I rarely wear suits.
Indeed, one could easily make the case for black loafers for even jacket wearers, provided their style is smart enough to be really functional in a wardrobe. Actually, I’ve started changing my mind first after seeing a pic posted on George Cleverley Instagram, and later on over a afternoon meeting with a guy at a coctail in an art gallery.
A process indicative that I read what was written about black loafers on the now defunct A suitable Wardrobe …
John

Tim

Personally I cannot stand the look of loafers, perhaps because the only people I see wearing them are strange alternative types, wearing some sort of gaudy mixture made up of menswear and high fashion, which is the last thing I want to be associated with.

Joe

Those critical of the black loafer might find this Die, Workwear! article interesting

https://dieworkwear.com/post/177782838244/the-sophisticated-black-tassel

Nick Hand

Hello Simon,

I agree with you (and some other readers commenting) about the usefulness of black loafers based on the fact they straddle formality scale. They immediately soften the look of a worsted suit in my (quite casual) office, and I particularly like wearing them going out somewhere smart in the evening – especially in the height of a Sydney summer. Even when tie-less and sock-less (to beat the heat), if polished up to a mirror shine they just add an extra touch of formality you don’t get with brown .

I often pack them when travelling on a city holiday as the “third”pair. The colour makes them more suited to when there is a fancy restaurant or more formal event to attend, and yet because of the style they’re still just casual enough to include in the daily rotation for visiting museums and galleries.

Nick.

Al

Hi Simon. Funny how much people are skeptical about black loafers. I guess it all depends also on the place you live. I am Italian, South of the peninsula, and I would say loafers are by far the most used dress shoes. They allow you to be “dressed up” in the hot climate we often have. So here you can see them used a lot even in the winter months. Maybe in other colder countries (such as England), where you can wear an oxford most of the year, they are not seen as elegant enough? don’t know. And, I’d adventure to guess, maybe you added two of them in a five items list thanks to your experience and contacts with different countries, including mine.

Dan

Simon, your thoughts on a pair of black suede penny loafers? E.g -https://www.skoaktiebolaget.com/products/enzo-bonafe-penny-loafer-in-black-suede

H

Really great article. I’ve worked hard over the past four years to create a little capsule collection of seven good Northampton-made shoes, but if I had the chance to start over I wouldn’t include them all. The black chelsea boot, my second purchase, was very questionable.

The black calf oxfords, the brown suede loafers, and the brown grain derbies are the three I take when I travel, although I adore my black tassel loafers. I like the dark brown oxfords and the black brogues – but they don’t get worn so much.

A question though: how do these Essenziale shoes differ to the English competitors in their price category (eg G&G, Edward Green, Fosters RTW) – both in terms of make and more importantly style?

James

I definitely second the versatility of the dark brown suede loafer.

Aside from the smarter look of the black calf, is part of the appeal that it covers instances where brown doesn’t quite work?

Black can still strike me as stark and formal. Where could a dark navy suede stand in the scheme of things?

Andrew

Hi Simon,
I am a complete beginner to the world of men’s style, on a tight budget. I’m just starting to dip my toe into building a collection of some more considered formal clothing for the occasions when this is required.
I wonder what your thoughts are on a brown wingtip brogue like this (https://www.loake.co.uk/torrington-antique-brown.html) for everything from a navy suit down to slim, dark jeans?
For the time-being, I can’t justify having more than a black cap-toe oxford for the most formal occasions, and a second pair of brown shoes, which need to be as versatile as possible. I noticed you wearing a similar pair with denim in this post (https://www.permanentstyle.com/2014/04/levis-final-bespoke-jeans.html).
I’m struggling to find clear information on what this second pair should be.
Am I expecting too much versatility from a single pair of shoes?

Andrew

Thank you. Of course, you’re right about the oxfords. There’s no need for these to also fill that role.

Would you recommend that I also avoid pairing these with navy chinos? I.e. is it the colour of the trouser that makes it an unsuitable combination; or the formality of a suit? I will likely be wearing these with chinos much more often than jeans, but can avoid navy if that’s not going to work.

I’m just looking for a second shoe that is as versatile as I can reasonably expect. It sounds as though these might fit the bill.

Andrew

Most of the time I will be wearing a sports jacket (mine are all in more textured materials: tweed etc), shirt and chinos. Occasionally I will be dressing down to jeans. I’m not sure I’m ready to go as far as loafers, but it sounds as though the wingtip brogues will work as long as I stick to my lighter coloured chinos (especially grey). I’ll keep navy to pair with my black oxfords.
It also sounds from another post as if I ought to be looking for a pair of grey flannel trousers. That’ll be next on the list!

Jens

Can you imagine a more casual outfit (maybe even with dark jeans) that could work with a dark brown balmoral cap toe or is this shoe too formal in order to be worn like that?
Thanks a lot in advance!

Jens

Thank you, Simon!

Michael

No brown suede Chelsea boots….. a must have?

Lindsay McKee

Chelsea definitely over chukka for me!!

Rafael Ebron

I ended up doing 1. black oxford (John Lobb Beckett’s) 2. dark brown loafer (John Lobb Kipling) 3/4/5 ended up doing bespoke Cleverley’s two in the red Russian a whole cut and a Churchill, and then did a brown de Rede loafer in their pigskin. Before all that though I had a reddish brown Lodger loafer which was great with suits and jeans (like all the ones above). Never really liked derbies, chukkas, and definitely not monk straps, the latter just felt too pretentious. The Cleverleys are awesome but next time I’d go for more walkable style since I’m 99% business casual with jeans. I’m thinking suede loafers with walkable soles for next time. The black oxfords do always comes in handy and the whole cut and pigskin are my favorites.

Charles Pennington

How do they cost?

James

Hi Simon, sorry if not relevant to this post but you mention denim in there and I am curious how you go about finding jeans that fit? I am also blessed/cursed with a small waist and large cycle butt and thighs and find it almost impossible to find jeans that fit. Do you get darts or any alterations?

Arthur

Hi Simon!

I do enjoy PS and especially this ‘5 Things/Capsule Collection’ series . I did have a few questions. What is the reasoning behind suede loafers being on the list vs. calf loafers? Would not the latter be more versatile, particularly in inclement weather? I ask this because I also saw your post on your Belgravia loafers and how you were going to acquire a suede version shortly.

Also, does it matter whether the loafer is a penny style loafer (which, I would imagine, would be more formal due to its lack of ornamentation – I.e. tassels) or a tasseled style? And what about other loafer styles, such as the butterfly loafer, those with elastic sides and seem like brogues, or the wholecut or slipper-style loafer, or even the Crompton from G&G?

I have a lot of shoes, but am now looking to do away with what is not ‘necessary’ and fill in gaps where they may be. Your thoughts would be greatly appreciated.

Mike

Hi Simon,
At number 5 you mentioned dark brown suede chukkas. What about brown leather or grain leather chukkas instead of suede?

Anonymous

Hello. I am looking at buying a pair of Edward Green ankle boots. I am between the Ravenstone buckle boot (https://www.edwardgreen.com/shop/shoes/ravenstone-dark-oak-antique-calf-202-last.html) or the Banbury lace-up chukkah (https://www.edwardgreen.com/shop/shoes/banbury-dark-oak-antique-calf-202-last.html), both in dark oak with rubber soles. Which one would you choose and why? Thanks in advance.

Mark R

Hi Simon,
I feel like you’ve stressed this again and again in this article, but i just wanted to definitively ask – i feel as though the advice is, basically, go with dark brown for 4 pairs, and one pair of black. Am i reading this correctly? The reason i ask is that i have dark brown chukka’s, dark brown tassled calf leather loafers, and dark brown derby shoes – my next pair are planning to be suede loafers – would you suggest sticking with the same dark brown (in which case all of my pairs will look the same), or is this an opportunity to go with a tan, for example, or a different shade? Many thanks.

Mike

Since he has 3 dark brown why not tan?

And why do you put a strong emphasis on dark brown over other colours?

Mark R

Thankyou Simon.
My office is very casual. Trainers or brogues are the norm. Black shoes are for only the smartest occasions.- Twice a year perhaps at best.

Sitanshu

Excellent article Simon. I completely agree with your top 3 choices. However, instead of brown chukkas, I would recommend brown leather Chelsea boots. Especially useful during winter months and go well with jeans too. And instead of the black loafer, I would recommend a tan monk strap. Primarily, because I find it difficult to match black loafers with jeans, where tan monk straps go well with jeans and can occasionally be worn with suits.

The black loafer though, would be the 6th shoe on my list.

Anonymous

Would a pair of vass penny loafer in dark brown museum (U last) smart enough to go with a navy suit / charcoal suit and casual enough to go with dark jeans? Cheers.

Anonymous

Would they work with black jeans?

BespokeNYC

I love these kind of articles, but am especially looking forward to the more casual version of this list. I can’t help feeling that black captoe Oxfords are only really essential for an ever-shrinking segment of men who wear a suit and tie to work every day. They’re just too smart for most other outfits. Even then, unless you work in the city (where people are weirdly obsessed with a shoe-version of “no brown in town”) you can pretty much always substitute in dark brown instead. I guess the only time they’re absolutely essential is for funerals, or if you happen to wear a lot of black suits, but neither of those seems common enough to be #1 of only 5 pairs of shoes.

Was also surprised not to see anything for wet/snowy weather. Perhaps swap out one of the loafers for some pebble-grain Dainite sole chukkas? Or some nice Galway boots?

Imran Khan

Hey Simon- I’ve been following your posts and articles and love the advice offered. In fact, when I’m making a purchase for my wardrobe or coordinating colors, I often ask myself “what would Simon do?” lol

Anyways, I’ve taken your advice to heart on shoes and have read every article you have. I have indeed found that dark brown is exceptionally versatile. However, the one color I find that also works well for me(although not as versatile) and adds some interest to my clothing style are dark burgundy / maroon shoes. I actually don’t like them with navy blue- I feel the red/blue contrast is a bit too much for me me- looks too colorful and noticeable. However, I find burgundy / maroon shoes match exceptionally well with charcoal trousers. It provides color contrast without being too start- hues complement and darkness is similar. Burgundy / maroon also works well with dark brown trousers- provides a subtle contrast v dark brown shoes… and black shoes in this case would be a no-no.

Alex

Dear Simon,

I have two questions. First, do you prefer a smart round or a chiselled toe penny loafer? Second, I love wearing black jeans, either with sweaters or smart shirts. Should I go with a dark brown calf loafer or a black calf loafer? (I personally dislike the look of suede.)

Kind regards,
Alex

Jan

Dear Simon, have you ever heard of Samuel Windsor? They offer a broad range of classic shoes, apparently Goodyear welted by hand using Italian leathers, for under GBP80 per pair! Clearly not the prettiest shoes around and I assume they are using the cheapest leather they can source and have their production where they can find the cheapest labour etc. but the price quality seems to be off the charts and a good proposition for people on a tight budget. Any thoughts / insides on how they manage to do this?

Jan

Thanks Simon. I agree and I am fortunate enough to have lots of better things in my wardrobe – was just amazed by the price for which they manage to do these..

Anonymous

For someone starting to build a wardrobe, do you recommend him getting an extra pair of trousers for each suit?

Anonymous

I am planning to get a pair of dark brown leather loafers with full strap alligator strap. Would they be similar to the ordinary dark brown leather loafers in terms of versatility? Thanks

Faheem

Hi Simon. This’s a great post. I’m wondering what’s the best pair of shoes to wear with jet black (skinny) denim jeans? I’ll be grateful for your advice.

FIDELIO

Hi Simon,
I am about to purchase the Edward Green Piccadilly in mink suede. On the website they only offer the rubber sole option though. What do you think of it in terms of versatility and durability? Should I go for leather soles MTO?
Thanks

Shem

Merry Xmas Simon. I have never worn and owned chukkas but have been tempted by the drakes Crosby moccasin style unlined chukka boots. I’m concerned how they will wear in a humid country like Singapore as I feel styles leaving the ankles exposed (eg loafer with no socks) makes a big difference in how hot one feels. Wanted to get your thoughts on this.

Shem

hi simon,

I may be pulling the trigger on my first pair of chukkas down next year and am deciding between 2 drake’s models which are in dark brown suede:
1) https://www.drakes.com/shoes/chukkas/crosby-moc-toe-chukka-boot-brown-suede
2) https://www.drakes.com/shoes/chukkas/clifford-desert-boot-dark-brown-suede

I’m keen on option 1 but am unsure how the moccasin style toe may affect the style and how it pairs with outfits. Is there anything to note if going with either options? Many thanks

Alex

Firstly, Happy New Year!
I had question re: Daninite vs Leather soles.
I recently ordered a pair of C&J oxfords brown with broguing. But am having second thoughts because it’s not a leather sole. It’s my first pair of shoes above £250. For the the price c. c400 should i be getting ones with leather soles. ?

Alex

thanks, Simon.
I want to wear them with suits but will also probably wear them with regular trousers/separates combo, .
I will also probably wear them in the summer.
These are the ones i ordered.
https://www.crockettandjones.com/malton-darkbrown-calf/
At that price and wanting them to be versatile should i be going for leather?

Aex

apologies predictive keeps turning Dainite into Daninite.
I also meant to say I want for formal as well as non formal occasions.

Anonymous
Anonymous

I plan to wear these once every other day. Do you think they will hold up well, given that they are unlined?

Anonymous

Since shoes need to rest one needs at least two pairs of business shoes. What would be the minimum number of shoes one should have in his business shoe rotation to ensure a good lifespan for each shoe? (wearing business shoes 5-6 days a week)

Oliver

Hi Simon,

This has been a very helpful post in building my shoe collection. I was wondering if you would consider doing a post on your first 5 boots. I’m trying to slowly build out a collection of boots for a business casual workplace/weekend wear, right now I have a pair of Dark brown chukkas and Red Wings but I’m not sure where to go next. Chelseas? Brogues? Balmoral? Suede or Calfskin or Grain next?
I think a separate post for a boot capsule collection would be helpful for many readers, especially those who have never invested a great deal in boots previously. Thanks!

Anonymous

How versatile would you say is a burgundy oxford (chinos, jeans, flannel, suits etc.)?

Is it as formal as a dark brown oxford or less?

Anonymous

Why wouldn’t you wear any calf oxford with jeans or chinos? Is it just your preference or would it be a faux pas?

Anonymous

Do you like navy suede derbys? Do you find them versatile?

Noel

Even if they are quite dark in a material like cordovan? From the distance they might look like black.

Rob

Simon, sorry another question. It seems from this and your other articles/photos that brown suede is incredibly versatile. On the basis of that I am going to try to find two pairs – perhaps a loafer and either a derby or chukka.

My question is one of colour. Very dark brown seems the most versatile colour. But two in the same colour seems a bit imaginative. Do you think I would get as much use from a slightly lighter brown or a brown with a slightly redder hue. For me it is all about £/wear.

Kind regards

Rob

Thanks, Simon (and also thanks to your reply on another article – there is far more information on this website than I imagined).

One follow up question – and apologies for sounding a bit needy. It relates to the spectrum between formality and informality. I can see that this is a function of style, material and details. It is very clear to me that an Oxford in black leather will be more formal than a loafer in light suede.

The point I am struggling with is the line between a less formal Oxford and a Derby. Could an Oxford in, say, dark brown suede with brogueing be used with cheanos or jeans? Would that be more flexible and useful than a Derby in dark brown suede, or brown leather? Could that Derby be used quite so well with a suit?

Many thanks

Rob

Rob

A typo above. I meant “unimaginative”.

Anonymous

Hi Simon

Do you think the below shoe in polo suede would work with jeans? I want to avoid dark brown suede as I have too many shoes in this colour, so want something a bit different. I quite like the idea of polo vs suede as it has a slight reddish tone. It might mean, it’s best suited to darker denim?

https://www.carminashoemaker.com/penny-loafers-brown-suede-80730

Anonymous

As always , thanks for the response. Would the below be more casual? Again in polo.

https://www.carminashoemaker.com/penny-loafers-brown-suede-923-eee

Joel

Simon,

What’s your thoughts on toe plates (triumph or lulu) on shoes? Specifically loafers.

Anonymous

Hi Simon, what dark brown calf leather penny loafer would you recommend at the Crockett and Jones price point? I have the Boston and am looking to try another another last that’s similarly round as the Boston. Don’t want shoes that are too similar, thanks!

Toby

Hi

I’d suggest Grantham II. It has the same toe shape as Boston but with a more clipped heel to minimise slippage; the apron is also cosmetically slightly different.
https://www.crockettandjones.com/grantham-2-darkbrown-calf/

Dan

Suede footwear used to be reserved for the chillier months of autumn and winter, or so I’ve heard. We’ve come a long way to move on from such hard rules and guidelines, but I was wondering if the color of suede was still dictated by climate. I’d like to purchase a suede loafer, either penny or tassel that can be worn throughout the year. Taking into consideration of versatility and its appropriateness to be worn year round, would you recommend dark brown or snuff/tobacco?

RT

Hi Simon,

I’ve wanted to buy some loafers for some time, preferably in brown suede, but in the past have not succeeded in finding a pair that I could keep on my feet. I seem to have particularly slim heels, but a fairly standard width foot at the toes, meaning that loafers that fit at the front slip excessively at the heel. The problem may be exacerbated by having fairly low arches too. I think read that you also have slim heels. Can you recommend any RTW loafers that you have found to be good for overcoming this problem?

RT

Thanks, Simon. I bought tongue pads recently for that very purpose. Hopefully, I’ll be able to get out to Edward Green and one or two there in the fullness of time and try some different lasts. I’m a little hesitant about going bespoke at this stage as I’m really well catered for in terms of oxfords and derbies and, cost issues apart, wouldn’t want to commission a bespoke last for a loafer, which may well be my first and only bespoke commission. Perhaps that”s foolish, though. As all my tailoring and shirts are now bespoke or very top end MTM )thanks in no small measure to PS) perhaps the next logical step is to extend that to footwear. Anyway, thanks for the advice. Food for thought.

Ian A

I have a similar problem with loafers RTW as one of my feet differs in length ever so slightly and the design of the loafer really shows this up! Some brands and models will fit slightly better than others but it is never wholly satisfying in terms of fit, hence loafers are mostly not for me.

RT

Thanks, Simon

Ian – I have the same issue with my left foot being slightly longer than the right (in addition to the slim heels). With the addition of shortish arms and a dropped right shoulder I think that I must have been assembled from random, left-over parts; perhaps late at night, with fatigue (and possibly alcohol) being a significant factor in the outcome…or perhaps my role in life is simply to test the skill and ingenuity of tailors and shoemakers 🙂 Apologies and sincere thanks to the tailors who endeavour to cope with my little idiosyncrasies with patience and courtesy!

Dan

Hi RT,

Sorry to barge in, but you might want to try Crockett and Jones’ lasts 375 and 376, which were developed specifically to fit the slim heels of the Japanese market. The Carmina Uetam last is also satisfactory for me, and although I’ve never tried, you may also want to look into Gaziano’s KN last or JM Weston which offer an array of widths.

The problem with going bespoke with loafers is that very few makers will agree to making one as your first pair.

RT

Hi Dan,

Thanks for the tip. I have oxfords, monks, boots and a derby from C&J, but none in the lasts you mention. I’ll definitely check them out. I’ll look out for the Carmina too. I’ve tried G&G, but still had the same problem, unfortunately. I think the bespoke thing isn’t a good idea just for loafers. I was hoping to try St Crispin’s modified last service, but I never got a reply to my email.
Anyway, thanks again for the tip re C&J lasts.
Richard

Dan

Hi RT,

An old thread, and I’m not sure if you’ll read this comment, but an Enzo Bonafe loafer (model EB 07) was on sale and I took the plunge. I have a very narrow heel, so much so that a London bespoke shoemaker recommended that I steer away from seamless heels since they couldn’t be able to guarantee a secure fit even on an oxford. The Bonafe afforded a surprisingly snug fit at the back of the foot, so you might want to look into them as well.

Toby

Hi RT

I have the exact same issue as you. Slim heels, low arch and moderate width. I have found C&Js’ Handgrade Cadogan Unlined Loafer (363 last) to be by far the best solution in their range. I drop down 1/2 a size compared to my lace-ups on the same/similar lasts.

Being unlined allows for the drop in 1/2 size and the reasonable length of 363 means there’s no issue in the toes.

Anything on 375 would be the next best in my opinion

Ayush

Hi Simon! Do you think I can wear oxblood shoes with charcoal grey trousers/chinos? And if not what would be your suggestion instead of ‘black’.

Ayush

So sorry Simon! I just thought that my comment did not reach you. Just saw that you have already posted a reply. Thank you so much!
Would take care of it from next time.

Christos

Who is the maker of the pictured brown-suede loafers? I like their toe shape!

Joe

Love articles like this, Simon, thank you: interesting, informative and helpful.

However, it does highlight what seems an increasingly large hole in my shoe repertoire: loafers. I’ve never been able to get my heard round them; they’ve always seemed a bit, well, ‘posh’. Ridiculous, I know, but such associations can hard to shake. Yet every single site and account I follow suggests they’re the cornerstone of a stylish (tailored) wardrobe. So I definitely feel I’m missing something.

I wonder if you might have any particular recommendations for a loafer novice? Penny or tassel? C&J or Alden (or EG)? Or just accept that they’re not for me, perhaps, and stick with a trusty chukka?

Joe

Thanks, Simon. I work in publishing so never wear a suit to the office; in my industry even a sports jacket has people asking if you’ve got a job interview. So something slightly more casual, to go with chinos, cords, flannels, sounds sensible.

Vincent L.

When you write “brown chukka” do you mean “dark brown chukka” ?
I saw a good chukka boot from Carmina, but it’s not dark brown, it’s close…I’m not sure if I should buy it because dark brown is better in the long term.

Anonymous

I have a question regarding toe shapes. I always wear cap-toe oxford shoes with a suit. But I only feel comfortable in classic round shaped shoes like Edward Green Oxford Chelsea or Crockett & Jones Connaught. Although I like these shoes a lot, I’m wondering if I do something wrong when trying on more elongated looking shoes. When walking elongated shoes feel too long to me and when the feet bends it feels like the leather is exessively cutting into my toes. It’s difficult to explain. How do you determine the right fit on more elongated shoes, Simon?

John

Hi Simon, i was hoping you would help me with two questions:

1) What is your opinion on full strap loafers? I am considering a pair of Anglo-Italians C&J (https://angloitalian.com/collections/footwear/products/crockett-jones-bradbourne-loafer-brown-suede) and have been looking online regarding people’s opinions on full strap loafers but have not been able to find anything sensible. My impression is that it is a subtle design point that is not worth over-complicating, but i am not sure how much a full strap changes the aesthetic of a shoe versus a conventional strap.

2) Does an all-suede shoe collection make sense? I always find myself drawn to suede as it traverses the boundary between smart and casual so well, plus i love the texture. Like many people now, i rarely have the need for very formal dressing (full suite) so i don’t really need a standard leather pair. But then again, is it abit boring to only have suede shoes?

Any feedback would be appreciated, and many thanks.

John

Thank you for your thoughts Simon, very much appreciated.

Decha Lertsumitkul

Excellent. That’s one thing I going through. A more casual to business experience. Maybe a oxford suede or monk strap.

Decha Lertsumitkul

I have a few oxford in black, dark brown,and light brown. My next purchase might be loafer or a monk strap or oxford in suede.

Stephan

Hello Simon,
what kind of shoe could be the desert boot/boat shoe in the fall? Both work well in spring/summer, when the temperatures are high and it isn‘t wet. A walk in the park or forest is easy possible with them. But in fall things look different…

Cheers,
Stephan

Stephan

Hello Simon,
I think of your article, where you presented trainers as alternative. Good for playing with the Kids in the park. Maybe there is something „dressier“ suited for the wet, cold and grey german fall. Or are there perhaps trainers for this time of the year? (I suppose, suede or cotton is no ideal material)

Cheers,
Stephan

Anonymous

Would you wear black leather Chelsea boots with a suit?

If the dress code is business casual, are chelsea boots acceptable with flannel trousers in the autumn/winter?

Nat

Hi Simon would you say that these rough-out suede chukka boots from C & J would be a too casual alternative to the dark suede chukka boots shown above https://www.crockettandjones.com/collections/mens/boots/molton-darkbrown-roughout/

I love the look but not sure that it would be as versatile as these
https://www.crockettandjones.com/collections/mens/boots/upton-darkoak-suede/

I would love to hear your thoughts.
Many thanks

Les

Hi Simon, like Nat above, I’m fan of how waxed suede looks and particularly ages. I certainly agree there are more versatile options, and regular dark brown suede will be better for smarter settings. However, do you think such a boot could look good with a brownish tweed jacket, PS OBCD, and the right denim? Cheers

Les

Very helpful, appreciate the nuance!

Michael

Hi Simon,
What boot would you recommend in a casual wardrobe for jeans, chinos,cotton trousers? Other than suede loafer and chukka boot? Perhaps a chelsea boot in a dark brown leather would work? It depends also on the last maybe a rounded toe than a chiseled or almond. What do you think?
Thanks!

Michael

Hi Simon,
Besides the shoes you mentioned what about some boots for winter? Do you think this boots from Crockett Jones can be worn smart casually? Jeans,chinos,cotton trousers,flannels?
Do you recommend something else?

https://www.crockettandjones.com/collections/mens/boots/coniston-darkbrown-scotch-grain/

Anonymous

I imagine you’ve probably seen DieWorkear’s latest post on shoes. In it, he mentions a rule which is new to me … no oxfords with less-formal-than-suit. Do you agree with this rule? I’m getting ready to purchase my second pair of nice laced shoes – Saint Crispin’s – and I was planning on a mid to dark brown oxford, thinking this would go with just about everything. I very rarely wear suits, bur rather odd trousers and sport coats, knits, linen, flannels etc.

I’ve never really cared for the look of derbies. Not crazy about chukkas or norwegians. I can always go with tassel loafers, but I was looking for something laced this time. I thought brown oxford was the solution. What do you think? Are oxfords too sleek and formal for odd trousers and sport jackets, high-low, tweeds, etc?

Anonymous

Thank you, that is enormously helpful as always.

(Different!) Anonymous

I hope that you don’t mind me commenting on this old comment, Simon.

Would your answer change if the oxford in question was in dark brown suede, rather than in leather – would that pair with jeans & chinos as well as flannels or would you still recommend a Norwegian?

Thanks.

(Different!) Anonymous

Cheers.

Norman

A pair of split toe low vamp full saddle strap loafers will go anywhere and with anything, black or otherwise you can do it! It’s called style!

John

This is an extremely useful article that i keep coming back to.

Simon, do you think EG’s Shanklin chukkas in mocha suede are suitable as a versatile pair of chukkas? In particular, given that they are unlined do you find that you can wear them in the winter? I am not so concerned about them being unlined as my feet easily overheat and sweat. Just curious to know how you find these boots.

Many thanks.

John

Thanks Simon, that’s very useful. Do you happen to have any recommendations for a pair of chukkas that meet the specifications you mention? Many of the chukkas I have seen are much more chunky with less shape, such as Crocket and Jones Chilterns.

Thanks again.

AG

Hi Simon,

Wasn’t sure where to put this comment, so apologies if another thread would have better. I have quite oddly sized feet (about 5.5 F/G and a very high instep) and have always struggled to get things that fit well from the low-mid range of what you cover.

I consequently visited Cleverly, Edward Green & GG recently (I’m London based) and all said that I won’t get a good fit with their RTW ranges, leaving the options of either bespoke or MTO. Given that bespoke is too much of a leap for me at the moment (I hope to build up a decent collection of shoes from one of these providers reasonably quickly, so £4-6k per shoe and a 12 month process doesn’t work), I wonder if you have any views on the MTO offerings of either Edward Green or GG? Is there anyone else I should
consider

EG’s shoes felt a little better in the shop and they seem to offer test shoes in their custom made process, but on the other hand GG felt less “salesy” (acknowledging that MTO may not give the perfect results) and seemed more willing to, e.g., personalise lasts…

Any thoughts would be much appreciated, so thanks in advance.

AG

Many thanks for the response Simon – just a quick follow up, if that’s ok.

It turns out that both EG and GG offer test shoes with their MTO and there is some scope for last modification (adding room around instep, pinky toe, etc). Given the 20% offer at GG, they’re also a similar price, so it looks like a toss up to me in terms of process / likelihood of getting something that fits… would you agree? Should I expect broadly the same quality shoe from both?

Finally, on style, they both recommend a derby or chukka given the shape of my foot and my preference for something fairly casual, so I am veering towards either a Dover or GG Stamford / Isham in suede. Is there much to separate either EG / GG’s offering in this style (e.g. in terms of versatility / working with denim & chinos)? I note that on blogs, etc, there tends to be a bias towards the Dover but the Stamford looks pretty similar to me…

Any thoughts would be very much appreciated!

MB

GG’s MTO service can have slight adjustments to the last (at least when you order in store). They added quite a bit for my instep on one foot and a small amount for my instep on the other (but made it in a wider fitting). I’ve never asked about EG’s MTO so can’t comment on that – I find their RTW more comfortable out of the box so it’s never been an issue (just an extra insole in one shoe and I’m good to go).

I’m constantly torn between GG and EG. I tend to go with EG because I don’t want something quite as dressy but I think there are more pairs of GGs that I look at and really want to add to my wardrobe. I think that’s because the shoes are a bit more eye-catching (often in very rich, beautiful colours) but that’s also why I end up thinking something from EG would be more versatile.

Both wonderful choices though. Hope you get something you love!

JFK

Simon, I am curious, is the black captoe in the beginning of your post any paeticular one? I really like the look of it and the form and I am curious which company made them!?

Michael

Hi Simon,
After reading many of your articles you convinced me to invest in quality than quantity ,buy the best I can afford and I bought my first pair of boots from Crockett and Jones. The quality is way higher than my standard shoes and now I am looking at a pair of chukka boots in suede.
The chukka boots will be part of a casual wardrobe or weekend wardrobe as you describe in your articles but sometimes I will wear them with cords perhaps flannels other than jeans and chinos.
Which out of these 3 models do you think is suited for this kind of wardrobe ? Does the last play an important role considering that one model has a chiselled toe?
Thanks!
https://www.crockettandjones.com/collections/mens/boots/chiltern-darkbrown-suede/
https://www.crockettandjones.com/collections/mens/boots/tetbury-darkbrown-suede/
https://www.crockettandjones.com/collections/mens/boots/upton-darkoak-suede/

Michael

Thanks for the help Simon.
You mentioned in your articles about shoes in suede for a casual wardrobe. But in my country sometimes it’s raining for days and I don’t want to wear a pair of suede shoes,I want to protected them as much as possible. During spring, boots are out of the question because it’s hot outside. Even though you said that suede can handle rain I was thinking at a pair of calfskin shoes. My wardrobe consists of casual clothing such as a weekend wardrobe,jeans,chinos,cords and sometimes want to dress up a little. Do you think a plain derby in dark brown calf would be suited as a pair for this wardrobe of a split toe derby in same colour would be better? I like the design of a split toe derby .
Thanks

Michael

Hi Simon,
So the split toe derby in calf or suede could work also with chinos or cords? Sometimes with cotton trousers?
Thanks and Merry Christmas! All the best!

WK

Hi Simon,

I understand you are a big fan of suede but how would you rate the formality between suede and grain calf leather such as Edward green Utah? It seems to me EG piccadilly in dark brown utah can be very versatile and the leather is also extremely soft like suede. Have you tried the utah leather of EG?

Thanks for letting me know your opinion!

MB

I have a couple of pairs in Utah leather. A Dover and a Cranleigh (in dark brown and burgundy, respectively). The grain is relatively subtle compared to county calf or London grain and these are the most flexible grain leather shoes that I have. I don’t think I’d wear either pair with a suit but then I don’t think I’d wear suede either. I would happily wear dark brown Utah with a jacket though.

I can’t comment on how flexible it is with different wardrobes but the Dover in Dark Brown Utah is my favourite shoe. The Utah leather is very comfortable and (for me) breaks in very, very quickly. Much faster than my calf or suede pairs.

As always, the best choice depends on what else you already have and what will go best with whatever you’re wearing! Hope you find some shoes that are perfect for you.

MB

I can quite understand that approach!

I confess that I wear suede less than most people here (I also don’t have any suits that aren’t primarily for business) and that might have an affect on my shoe choices. Perhaps more telling, however, is that most of my jackets are at the casual end of the spectrum (tweed or similar). The sort of thing that might go with jeans if made with less structure. If I’d (more sensibly) started my collection with a nice navy sports coat then I might think Utah rather less flexible!

Antony

Hi Simon, I was wondering what colour do you have the Cranleigh in and if it is suede?

Pradeep

I have read a couple of articles of yous on ‘shoes’ and oftentimes you have mentioned a ‘person needs to make sure that his shoe is one or two shades darker than the trousers’.
Do you use any special method to identify whether the shade of the shoe is darker than trousers or do you go with your instinct?
It would not be difficult to select a shoe when trousers would be on the lighter side but perhaps when it is ‘navy or dark brown or charcoal grey’ then it becomes a bit problematic.

MB

I admit that I find this harder when buying online (for example, I find EG’s website is almost always inaccurate from a colour perspective (half the shoes look too dark and the others too light). If going in person is not possible then I try to look at photographs from a wider range of sources.

By the time I own the shoes though it’s just a case of having a look!

Pradeep

Hi Simon!
https://www.rapawalk.com/product/1896/. This is the link of the shoe i am going to buy. Do you think it is dark enough to work with dark brown shoes

Pradeep

Very sorry i was saying dark brown trousers.
Your suggestion would be highly appreciated.

Pradeep

Hi Simon!
I asked a question yesterday but not able to find the answer to it. I think i might have failed to post it and so apologies if i am asking it again.
Can i wear black penny loafers with charcoal grey chinos?

Michael

Hi Simon,
I am considering to buy a loafer in suede on a casual last like Alden as a go to shoe, except winter I wouldn’t wear it.But I found in UK only the unlined version LHS. Would a unlined loafer last less than a lined one? And a unlined loafer is suited only for spring and summer,yes?

Thanks

Michael

One more question Simon,
Did you took your regular size in LHS Alden? I too have a narrow heel and wide feet at the toes like a V shape.
Thanks

David

I would be interested in your comments on the merits (or otherwise) of the plain-toed Oxford, such as the EG Curzon. Are they less formal than a cap toed Oxford, or just a shoe that is worn by those who wish to look smart, but do not know any better, so best avoided?

Greg

I’m torn between the Alden chukka in snuff suede (https://www.trunkclothiers.com/products/alden-unlined-chukka-snuff-suede-1493?variant=15418635255843) and a Drakes Desert boot (either https://www.drakes.com/dk/shoes/clifford-desert-boot-tobacco-suede or this https://www.drakes.com/dk/shoes/clifford-desert-boot-light-brown-roughout-suede-with-rubber-sole) – but am curious about versatility, quality (particularly crepe sole versus leather)…I don’t have a desert boot/chukka so this will be my first… better to stick with brown suede or tobacco/snuff. Any inputs welcome. Thanks a million

Greg

Thanks Simon!

Pradeep

Hi Simon!
Do you think dark brown suede loafers would go with charcoal grey trousers and also dark wash denim?
I am asking this question because i do not dark brown sueded to be as dark as maybe a dark brown leather shoe, and therefore your rule that a shoe should be darker than your trousers would not be possible.

Brandon Bennett

Hey Simon, I’m considering upgrading my (too small) To Boot NY half brogues that serve as my single pair of brown dress shoes with these Edward Greens that Sid M suggests. If you needed a staple pair of brown dress shoes that would cover almost all your bases, would these Chelsea cap toes be it? Thank you!
https://www.sidmashburn.com/dark-oak-antique-edward-green-chelsea-cap-toe.html

MB

I have that exact shoe and it doesn’t work well with most of my suits but would if it were darker. In some ways, I wish I’d bought it in a derby (like the Dover) as I think it would serve me better in that configuration but that’s largely a function of what I wear when not in a suit.

It’s still a beautiful shoe, just not as flexible as I’d originally hoped!

Ferdinand

@MB: I had some pairs of shoes recolored from a lighter or reddish brown to an espresso color. If you find a skilled artisan going from light to dark really isn’t much of a problem. I think here on PS I also saw a post on recoloring. Certainly doesn’t do any harm to the shoes. If you’re in Western Europe, I had it done via mail by Theo Frijn in Amsterdam (I am not affiliated in any way, just a very happy customer.)

Ferdinand

Ah, I see, thanks for the link! It seems like you weren’t really happy (“Difficult because the painting will never replicate the uniform finish of a dyed skin (…)”). I would agree that the color looks a little different, but when done well it reminds me of the hand-dyed crust leather used in some bespoke – in fact, I very much like the look. But maybe I misunderstand and you were more dissatisfied with the effect of the burnishing.

Brandon Bennett

Thanks, Simon! (On the Edward Green site, it looks darker and says it complements both navy and flannel suits. Though I’ll ask.)

Karol

What type of black loafer would you recommend? I don’t wear suits at all, mostly from casual to jacket and flannels. But since there are a lot of “cold” colors I like, I’d like an alternative to brown suede. Black suede probably won’t cut it, since it’s a bit visually heavy. Should I look for black calf tassel or penny loafer?

fenvig

Hello there Simon,
I am curious if you will reply on this old thread, but I have a similar question.
I’m looking to buy another pair of loafers and I own following four pairs atm:
Penny loafers (brown calf and dark brown suede) and tassel loafers (snuff suede and dark brown suede).
I want to buy another pair, but I could need som guidance!
I’d like something calf, probably with tassels and not brown.
Will you recommend tassels or not? Black or burgundy?
I guess black ones can be justified as I have four brown pairs, but will burgundy be more versatile as I am most often casually dressed in cords, flannel or denim?
Thank you 🙂

Ken

Much obliged for posting a very informative article, Simon!
I wonder if a pair of black Chelsea boots can be worn with suits in a very “strict” office like the London City jobs as an alternative of a black capped-toe oxford?

KEN

Thank you so much for your prompt reply, Simon!
Then I will go for a simple back oxford instead of boots.

Dash Riprock.

Hi Simon I have 14 pairs of shoes ranging from Henry Maxwell Dover st.1971 Tuczeck Jermyn st. When they were closing down 1969. To Rossetti,and Charles jordan. all loafers.2 with tassels church,s Melbourne and Kipling. I have one pair of Yanko brown suede Norwegian toe with laces .never worn. Must try them one day.

Rob

Has your opinion on shoes changed with the addition of cordovan shoes in your wardrobe?

John

Hi Simon, can i ask your opinion of the St. Crispin’s suede chukka you own versus the EG Banbury in brown suede? They are similarly priced and was wondering if there is any strong differentiator between them, in terms of quality (assume not) or shape of last? Which do you prefer?

Neither are cheap, but i have concluded that a brown suede chukka is so useful that it is worth dropping abit more money on. Many thanks.

Anonymous

Simon, would you say that the SC boots’ versatility is reduced due to their relative smartness? For instance, would you wear them with denim and/or chinos? Or just smarter tailored trousers? Thanks.

Peter

Simon – how do you feel about wholecuts in general, outside of the context of a 5 shoe capsule collection? Is a black wholecut Oxford flashy to you? Would you only wear it with suits, or could it pair with a smart sport coat and trousers? You don’t write about the style a lot. Not something in your closet? Thank you.

Chris

Dear Simon,
I am considering some shoes here for me wedding ( to accompany a dark blue bespoke double breasted worsted suit).
Am probably going to go with the Edward Green Chelsea Oxford in Black (the one with the cap toe). But had also been thinking of the Crockett hand grade Audley or possibly Belgrave (the cap toe with broueging). Would love to know your thoughts on if you had a preference? Was also curious if you thought a black cap toe was a bit too business for a wedding?
Thanks as always Simon,

Chris

Thankyou Simon.
Invaluable advice as always.

Michael

Hi Simon,
Do you think this Crockett Jones shoes could work with tailored cotton trousers since the shoes have dainite rubber sole?
Thank you

Peter

Wow really? Simon, you don’t think a double sole EG Dover works with a jacket? Thanks.

Peter

Got it, no split toes with suits! But not even a cotton suit? Or a casual suit – Neapolitan, patch pockets, plaid? How about, no split toes with worsteds! Thanks.

John

Hi Simon, may i ask for your advice regarding my own show collection? Currently i have:
1) Alden LHS loafers, snuff suede
2) C&J full-strap loafers from Anglo-Italian, brown suede
3) Cheaney brogue derby, brown suede (bought in a sale for 200 GBP, and very comfortable)
4) Grenson white leather sneakers (not as sleak as Common Projects, but half the price)

I am now either going to add Edward Green’s Dovers in brown suede, or Saint Crispin’s brown suede chukka (same as yours, though RTW), as i think the above lacks a general all-weather shoe for walking around town. My inclination is towards a chukka (especially given your various comments about their versatility) but was wondering what you think. Sorry to ask a question so focused on my own wardrobe, i hope that’s ok.

My ultimate aim is to have a small highly versatile wardrobe, not an extensive one. So i want all my purchases to count.

An unrelated request, at some point it would be great to see an article(s) from you that explores: 1) your experiences (positive and negative) around the inception and design of PS products. Things that worked, things that didn’t etc., even difficulties of working with suppliers, 2) PS items you are most proud of, or you feel are particularly unique/useful. Basically abit more insight behind the process and success (or failures!) of PS products.

From my perspective PS products are a huge hit as they guarantee versatility, quality and usefulness. I can imagine you don’t want to push too hard for fear of it looking like a sales push, but something about your experiences could be extremely interesting. Thanks!

John

Thanks Simon, i appreciate it.

Related to this, i saw on IG yesterday that you had a look at Edward Green’s new Chale boot: https://www.edwardgreen.com/shop/chale-mocha-suede-slim-rubber-soles-r1.html

How do you think it compares in terms of the last and aesthetic to your Saint Cirspins boot? It looks like the Chale fills a nice gap in EG’s boot range; more formal than the Shanklin, but not as heavy as the Banbury. The Saint Crispins are abit more sleek than the Chale?

Many thanks.

John

Thanks Simon, that’s helpful.

Bjoern

Hi Simon, for a versatile shoe collection the difference between calf vs suede is obvious. Another factor that determines the smartness of a shoe is it‘s last shape. I feel your readers would benefit from deeper exploration of this ground, maybe in a dedicated article and as addition to my favorite articles, the ones that cover capsule wardrobes. Here loafers and chukkas are frequently mentioned (capsule, shoe capsule, weekend capsule) as most versatile because they cover a wide area of formalities.
As an Example I really like EG Belgravias, but without having worn them they seem to be on the smarter end of the spectrum (last-wise) so borderline ok with denim?
Apart from that, can you recommend a North Hampton made chukka Boot that‘s Last works with Denim, Chinos and Flannels, so a wide range of said formality levels?
Or should a weekend chukka last differ from a business casual chukka?
I hope my nerdy questions are of value for other readers as well.
Thanks and Regards,
Bjoern

Chris K

Simon,

true to my word, earlier in the year I picked up my first bespoke suit (Navy, single breasted, 13 ounce or so worsted). A few lessons learned but overall very satisfied with it.

So of course my next port of call is a pair of black Oxfords. Now, I’m willing to splash a bit, considering how fundamental a pair of black oxfords are in a mans wardrobe. I’ve been back and forward between various makers, but keep coming back to EG, they know how to cut a fine shoe. In particular, the Chelsea (I particularly like the look of the 915 last).

In your opinion, if you were to have one pair of black Oxfords, disregarding bespoke options for a moment, do you think these would serve you well?

They are likely to be worn VERY infrequently (unfortunately, as is the suit, as a result I can’t ever see the need for more than 2, 3 at a push worsted suits in my wardrobe) this presents a little bit of pain, because the money could be spent elsewhere on things I actually wear day to day. However, I’m willing to invest with conviction and also with no regrets, knowing I have a trusty pair to call upon when the occasion presents itself. Would love to know your thoughts, as I know you’re well acquainted with Edward Green.

Ck

Chris K

Thanks Simon, appreciate that. Crocketts Handgrade is something I think I will look at. Certainly the lower price, but still solid quality, makes the whole thing much more economical for me.

Chris K

Simon, just a quick follow up. Your words reverbarated around my head for a while and I’ve concluded, C&J hand grade is my best option. The extra hundred that would have been spent on EG, much as I like them, could more effectively be spent elsewhere. Something that will get daily use.

https://www.crockettandjones.com/collections/mens-oxfords-collection/products/egerton-black-calf

Just wanted to get your thoughts on the Egerton as a one and only (for the foreseeable) black cap toe?

Ck

Matthew W

Hi Simon,
I am looking for a dark brown oxford to fit box #2. I really like Stefano Bemer’s example shown but it is somewhat out of my price range.

I am looking at Crockett and Jones (or similar price/quality range), and tried on the C&J Westfield (https://us.crockettandjones.com/products/westfield-darkbrown-calf?us=yes). It felt great but I am not sure if the extra broguing on the toe cap would make it too casual for a “one brown oxford” shoe collection. As I understand it, Stefano’s example is a quarter brogue and the Westfield would be a half brogue oxford?

Do you have any suggestions for similar quarter brogue styles to Stefano Bemer’s, or opinions on half/quarter brogue in general? The shoes would be worn most frequently with trousers/chinos, and would be the go-to for my navy and grey suits.

Thanks!

Matthew W

Thanks Simon (as always, appreciate your quick responses!),

My first thought was the Westbourne, but it is Chestnut brown and not the dark brown I thought would be more flexible. Thoughts on the colour difference?

(https://us.crockettandjones.com/collections/mens-oxfords-collection/products/westbourne-chestnut-calf)

Being in eastern Canada I have only found one store that stocks C&J and they don’t carry all models, hence why I tried the Westfield.

Might just be best to wait until my next trip to the UK

*And thank you Jonas for the alternative suggestions!

Jonas

Hey Matthew,

If you are going for something in the same price range as C&J Benchgrade, I would suggest that you have a look at the TLB Artista range:

Plain cap toe: https://www.skolyx.se/en/tlb-mallorca-artista/733-48881-tlb-artista-plain-cap-toe-oxford-vegano-dark-brown.html

Quarter brogue: https://www.skolyx.se/en/tlb-mallorca-artista/604-44916-tlb-artista-brogued-cap-oxford-vegano-dark-brown.html

Tom

Hi Simon,
How would having a brown calf penny loafer with texture affect its versatility?

For example, with the following:

https://www.johnlobb.com/en_us/mens-shoes/lopez-tensile-leather-sole#selection.color=Burnt%20Umber%20Moorland%20Grain&selection.shoe_size_mens=6&selection.width=E

Or with the EG Piccadilly with dark brown London Grain:

Could you wear either of these shoes with shorts, jeans, chinos, all the way to tailored trousers with jackets? I feel the trend towards more casual clothing has accelerated in the last year.
Thanks

Gab

Hi Simon, how would you rate Stefano Bemer’s RTW quality, for instance if compared to EG? Apologies if this has already been adressed but almost 300 comments 🙂

David

Are there currently any retail shops carrying Stefano Bremer in London? Looks like there have been some in the past but I cannot find any current ones. Otherwise, looks like a trip to Italy may be in the future, as I prefer to try shoes on,

P.A.

Hi Simon,

I have a pair of wing tip brogue oxfords in gold colour that is a few years old.
Retrospectively, this pair would have been more versatile in medium or dark brown.
Would it be possible to dye the shoe and have it looking great, or is it a certain way of ruining it ?

Thanks
P.A.

P.A.

Thank you for your quick anser. Considering that those shoes were relatively cheap, I think I’ll keep them as is, especially since I was able to give them some patina with shoe polish.

As for the dark brown pair, which would be more versatile : minimal broguing such as only on the toe cap, or an adelaide, or no broguing at all ?

P.A.

Their primary use will be to go with suits or tailored grey trousers and jacket, so I thought either adelaide or just the line of the cap toe being punched. On the formality scale, where would you put adelaides ? I like the design but am not sure how to place it in my wardrobe.

Martins

look up patina pictures where “patina” is stripes, looking like a botched paint job running length of the shoes. nowadays it’s called “art” but painting shoes like this is super easy. if you want uniform colour it’s harder… but easier with dark dyes. I’ve done 3 pairs for me, but I wouldn’t take up a 1000£ shoes. only if it’s a case of do it or ebay-rubbish it (didn’t make sense to pay what, 80£ to dye 130£ trickers. might aswell look for new pair on sale). end result is the colour you start with mixed with dye colour. (so light brown + purple might not get you purple end result as an example)

P.A.

Thanks Martin. As you say it doesn’t make sense to me to pay 100€+ for a good uniform patina when those shoes were bought 3 years ago under 200€. I might as well get a new pair.

Martins

Why don’t you try yourself? Strip all wax and cream, and as much colour as you can, get Fiebings leather dye from eBay and some cheap (but preferably wider brush). Have fun. Afterwards don’t forget to put as much moisturiser as shoes can take (for me it allways was A LOT). If you get it wrong, can allways turn it black.

P.A.

That’s a good idea, I used a dark brown Saphir cream and they already look a shade darker.
I might just follow your recommendations, as I hardly wear them.

Chris K

Simon,

best place I could think of to ask this question. Yesterdays Instagram teaser of the EG waxed suede collection caught my eye. I’m curious, where on the list you would place a pair of waxed suede Chelsea’s? Also assuming here, the brown would be the more useful?

They appeal to me because they seem like they’d be quite useful for my lifestyle. Knitwear, denim and waxed suede. leather or raglan, knitwear, flannels and waxed suede? or would flannels be a push? Would appreciate your thoughts as to how you’d wear them, this always gives me a starting point. I know C&J do a nice waxed chelsea as well, but I’d certainly be willing to go the extra few miles with EG, knowing the wear they’d get.

Ck

Chris K

Thanks Simon, lovely breakdown as ever. I do like that aspect of them, and have done for a while, something clean and modern about it, yet juxtaposed with the slightly rugged waxed suede.

The last question I need to ask, if you were treating yourself to a pair of EG, would you find these or the cranleigh in regular suede more useful? The cranleigh boot really does seem versatile across the more casual realm.

Chris K

Simon, just to add one last point to this thread. I’ve found, finding a clean derby/split toe boot like the Cranleigh (or Galway) in dark brown suede to be particularly tricky, from UK makers anyway which is what I’m interested in for these, other than EG who have plenty of options. C&J have one this season, but it’s a slate suede rather than dark brown, plenty of rough out options and regular calf but suede is lacking.

Do you reckon this has a lot to do with suede’s reputation as being ‘tricky’ to care for and as a result less consumer demand? It’s been said numerous times around here, and it’s true, it’s EASIER to care for than calf leather in many ways, with a simple weekly brush and occasional full maintenance.

Ck

Chris K

Precisely Simon. I was looking for a cheaper option than EG, and that’s exactly what I’ve run in to. It just means saving a little longer, which is no bad thing now I think of it.

My best,
Ck

Anonymous

Simon,

Thank you for your great website.

I have read about a menswear rule that oxfords should only be warm with city suits.

What do you think of this rule? Should it be broadly followed or added to the rules and how to break them list?

Thank you.

Tony

Hi Simon,

Thank you for doing the wardrobe building series; it helps a lot for me personally. I have a question regarding the brown suede loafers. If this is my first pair of loafers (I own a few pairs med/dark brown oxfords, a tan Russian reindeer Adelaide, and a pair of dark brown suede Oxfords), would you consider going for a darker brown shade of suede or a polo brown? Thank you in advance!

Best,
Tony

Tony

Yeah, I have a thing for dark browns haha. I live in Boston and I do a good amount of walking. Should I opt for a city sole instead of JR with toe taps for the winters and the amount of rain here?

Tony

That is the plan! The only pair I have for the rain currently are the dark brown suede oxfords. And beside my white sneakers, the only these dark brown suede oxfords are the only thing I could dress casual a little (probably should’ve gone for a chukka instead of suede oxfords). So I’m hoping this brown suede loafer will knock out both birds with one stone.

Jackson

Hi Simon

Not sure if you have answered this question anywhere before or if you necessarily have an answer, but I recently bought two pairs of suede boots. One pair of C&J chukkas and a pair of C&J Chelsea boots. Both were very supple and smooth and after having brushed them a couple of times, they now seem hairy and fuzzy and have lost the quality that made them quite so attractive. They look old. I’ve been calling cobblers, none of whom seem to be able to offer any kind of suede refurbishment service and I’m rather despairing that the two new pairs of boots I’ve got here are ruined within the first two months of owning them…

Do you know if there’s any way of restoring suede when it goes like this or is this a sign that I brushed them far too hard?

Jackson

Jackson

I think it’s possible I brushed too hard, but I would say my brushing was firm but considered. I didn’t go to town on them by any means.

if I brush in either direction it is still quite hairy. Lots of fibres almost looking like loose threads or leg hair bristling on the surface. I’ve read online that taking a blow torch to the surface can deal with this quite easily without damaging the shoe though it will remove the nap. Does this sound rather suspect to you?

Jackson

Seems like the way to go – thanks again!

Joel

One thing I would suggest to even the map is the Saphir Renovateur spray for suede. They have colored versions and they really do help restore the sheen and nap of suede. Also, a pig bristle brush like this helps brush the nap without being to harsh:

https://www.kirbyallison.com/wellington-deluxe-suede-cleaning-brush.html?queryID=ec7dbfb55b66c201004827b54e43325e&objectID=106676&indexName=prod_default_products

You could also try a fabric shaver to cut down some of those longer naps of suede.

Rui Lima

Dear Simon,

Would you consider swapping the suede chukka boots by suede jodhpur boots? Do you agree the latter is smarter though still casual?

Joe

Hi Simon,

What do you think about color 8 cordovan oxfords? Could they be as versatile as the shoes you put as first and second in this capusle? Does the oxford style work with the rather less formal material?
Best
Joe

Ron

Hi Simon,

I struggle with getting the right fit for loafers. I have (at least I think I have) slightly wider feet. When following traditional guidelines to buy loafers half a size smaller than normal shoes, this is too tight for me at the sides. However, when buying the same size as my normal shoes, I always experience heel slippage.

Is there any advice you can give on this? Do you maybe know a brand (Morjas price-range) that offer suede loafers with a slightly smaller heel?

Or do you maybe have another tip/workaround?

Thanks in advance,
Ronnie

Ron

Hi Simon,

Thanks, I did not see the loafer article before. My apologies.

I will ask a local shoemaker if he can put in half insoles or heel pads at the back. Living with the slippage usually means blisters for me.

Do you have any experience with heel pads over insoles? Just trying to go for the best option…

David

I’ve tried on Alden shoes and boots in the Barrie last and know it fits me well. I’ll check out the chukkas in the Leydon last but wanted to see if you thought the suede chukkas at the link below would work with grey flannels or does the sole make them too casual?

https://aldenmadison.com/collection/chukka-boot-brown-suede-1273s/

Thanks! Enjoy your website.

Michael

Hi Simon,
I am looking for a shoe suited for workwear clothing ,jeans, wide japanese chinos or trousers reproduction etc. A pair of boots is an essential part for this type of clothing but they are suited more to Autumn and Winter. What about Spring or Summer? Could a derby in calf dark brown leather but with a wider last work? For example, Alden Plain derby or Crockett Jones Lanark 3?
I am interested in your opinion. Thank you!

Michael

What do you think of Paraboot Avignon in calf? Is that shoe suited for this kind of clothing? I do like a quality shoe but I guess Paraboot it’s not at the same level with Crockett and Jones.

Michael

I know it’s not the place on this page but because I started to talk about this type of workwear clothing,may I ask what kind of belt would you consider for this type of clothing? I was looking at Silver ostrich belt but then I don’t think they would work with fatigues for example.
The Real Mccoys has a cowhide belt but it’s light brown.
Any recommendations or brands?
Thank you Simon!

Ian A

I own the Lanark 3 in black calf but thinking of the silhouette of the shoe and the wider Japanese type workwear Chinos I think you’d be better served by something like the Paraboot Chambord or Michael! The Crockett and Jones calf is still a little too shiny and the shape of the shoe still too elongated to give you what you want.

Michael

Thank you for your reply.
The Michael or Chambord looks too chunky that’s why I opted for Avignon.
Simon, what do you think of Alden Norvegian split toe in cordovan vs Avignon? The cordovan does seem showy. What brands could you recommend?
Thank you

Michael

Hi Simon,
After some searches I found this Alden NST from Frans Boone. Since I will wear wider cut jeans ,chinos maybe some fatigues like Orslow or Warehouse could these shoes work with these kind of bottoms?
https://www.fransboonestore.com/products/alden-nst-derosa-blucher-in-8

Thank you!

Henry

Dear Simon,

Your works have certainly aided me a lot during the journey of building an appropriate business casual wardrobe. Thanks.

Regarding point 2, dark-brown oxford, I’m facing a bit of difficulty. I’m now owning a pair of dark brown wholecut oxford by Carmina, and currently enjoying them pretty much. I wear them with navy suits and Sports coat/odd trousers.

I’d like to know, however, is it in your opinion necessary to acquire a pair of dark brown cap-toe oxford.

Henry

Simon, thanks for the quick response!
As I‘ve read, semi-brogues are fine. I’m eyeing on a pair of C&J semi-brogue. There is, however, a medallion on the cap. Wondering if it’s too much in this case?

John

Hi Simon,
What pair of shoes would you recommend for a not so smart office dress code (chinos, wool trousers, shirts, knitwear, and only occasionally sports coats), for someone who already has black/brown oxfords, brown calf (relatively smart) loafers and brown suede loafers? Except for the suede loafers, the other shoes feel a bit too formal. Maybe brown calf loafers with some grain? Cordovan? Or maybe brown suede or calf derby shoes would come next?
Thanks

John

For cordovan loafers, would the LHS in color 8 be a good pick?
And what would be a good versatile chukka in brown suede (for a not so cold weather, to wear as year-round as possible)? EG Banbury, or maybe Shanklin?
Thanks again

John

How do you find the fit on your Aberdeen and Harvard loafers currently, after wearing them for a while? Perhaps as a less forgiving material, could one make the case for a more casual and roomy style when wearing cordovan? Maybe as a winter counterpart of your suede LHS, for jeans and thicker workwear chinos?

John

Does the Banbury go well with more casual sports coats, despite its dainite soles?
Thanks!

Michael

Hi Simon,
I am looking for an alternative to boots that could work with wider cut jeans ,chinos etc. and I found this pair of Alden
https://www.fransboonestore.com/products/alden-nst-derosa-blucher-in-8
But I have a hard time seeing how to wear them.
Perhaps I can wear a pair of wide cut jeans still dark indigo ,throw a light grey Merz B Schwannen sweater and a M65.
Or perhaps swap the M65 with a peacoat.
Could they be worn like that? At the bottom spectrum of formality?
I am having a hard time to see up to where I can wear them on a lower end of formality scale.
Could you please help?
Thank you Simon!

Seth

Hi Simon, great article. I wonder if I could ask for some advice. I’m new to building a shoe collection. So far I have a Grenson black Oxford that I tend to wear with formal tailoring.

I work in the creative industry, so informal dress style and mostly wear jeans – I hardly ever wear a suit unless it’s a wedding or funeral. If I wear a jacket, it’s more casual – think slightly arty vibe. At the moment, I usually wear ETQ trainers or something like that in winter, or Vans/converse in summer, but looking to elevate my footwear a bit without going too formal.

So I’m looking for footwear options for smart casual jeans/jacket type combos. To cover most bases I’m thinking:

1) Dark brown suede derby. Something like this (https://www.drakes.com/wayford-plain-toe-derby-shoe-brown-suede) although wondering if a leather sole would allow me to dress the derby up a bit in a pinch.
2) Desert boot like this (https://www.drakes.com/clifford-desert-boot-tobacco-suede). I also looked at Loake’s Sahara desert boot and of course Clarke’s.

My question is, are the suede derby and suede desert too similar (in the crepe sole) to justify both in a capsule wardrobe? As I said, I’d be wearing with indigo jeans/shirts, sometimes with a relaxed jacket over the shirt and other times with a crew knit.

3) After that, I’m thinking that a brown Chelsea boot would be a good winter option to wear at the weekend with everything. Something like this (https://www.loake.com/product/huxley-chestnut-brown/) with a rubber sole that makes it much more casual and handy in winter rain. Although, I do have a pair of dark brown Blundstone’s for winter weather they are very practical and chunky.

I also wonder if I should consider a brogue shoe for smart casual although for some reason not so keen on the detailing (for my look) but admire them on others.

Any thoughts would be much appreciated. I guess I’d just like reassurance that I’m heading in the right direction!

Seth

Hey Simon, thank you! Well, I’d love to go for loafers but I suppose I feel self conscious about the style – like you spoke about with your black leather jacket – and also because I associate them with older gentlemen. But I could be tempted to give them a go. Would a dark brown penny loafer be the most versatile? I imagine if I tried them I’d probably love the convenience/comfort of them. Maybe I should just think of them like a more grownup version of my slip on Vans.

One other question if I may… I’ve heard you mention that shoes should be a shade or two lighter than the trousers when worn with tailoring. Does the same rule of thumb apply to wearing shoes with denim, or is that a different thing altogether?

Seth

Typo above *darker* not lighter

Seth

Thanks, Simon. Yep, at least some of this info is sinking in. I really appreciate all of your articles. I’m learning so much!

Kwan

Hi Simon,

I have been wearing dark brown chukka boots all year round in London without any difficulties caring and matching around my outfits. Now I am considering investing one more boot from EG, Banbury in taupe, but I was unsure how this colour would work all year round in London.

I was wondering if I could ask your opinion regarding this if you know this colour from EG?

Thank you.

Avnesh

Hi Simon,
second all the comments about how useful these lists are- thank you. For a more smart-casual capsule, would you recommend a Chelsea boot (eg RM Williams)? I can’t quite work out why you don’t seem to recommend them as I thought they might bridge nicely across chinos/flannels/jeans. Advice appreciated!

Avnesh

Thanks for such a prompt and clear reply as always Simon. This is a truly unique aspect of your site!

I see the point about the sleek/showy aspect of Chelsea boots.

Actually I wonder if that sleek/showiness is what is making me nervous about boots in general. Is it also a risk with the service boot? (Viberg or your Wolverines style)

It seems less of a risk with a suede chukka/loafer; but I wonder if a service boot might be a good option for the drizzle-afflicted London parent. I’ve wrecked too many loafers in the rainy parks of Zone 2 London, and am nervous to wear nice Alden chukka’s for these occasions. On the other hand, sneakers don’t quite seem robust enough. I think that is what was driving me to Chelsea boots, but perhaps a service boot is a less flashy option?

Kyle

Hi Simon,

I was wondering how many shoes would you bring with you to travel and what styles? I would think a pair for the actual travel, two for walking around and at least one pair for formal occasions.

Kyle

Could you give me an example of the shoes you would wear for each type of trip? Thank you for all your responses.

Amit

Hello Simon. I was looking at these https://row.crockettandjones.com/collections/unlined-styles/products/harvard-2-darkbrown-suede and https://angloitalian.com/collections/footwear/products/desert-boots-chocolate. Since I’m more inclined and have a soft corner for boots I prefer going for the latter. I’ll be mostly wearing it with jeans only in hot-humid Indian summers as of now and an all year round boot. I also think in terms of functionality, it’ll serve the same purpose but will boil down to a person’s personal choice and preferences. Always happy to know your thoughts and plan my capsule wardrobe choices.

Amit

Hello Simon. I’m looking at these https://www.yuketen.com/shop-last-pair/santiago-fo-snuff as my first pair of desert boots to wear with my jeans (all seasons in India). I still do like the Anglo Italian desert boots as well but as a matter of personal choice and preference, I’m leaning towards the former. I intend to wear the Yuki’s at public events and occasions with my Nigel (Indigo) and The Real McCoy’s (Blue) Jeans with PS denim/oxford and tapered tee. Let me know your thoughts on this one? It’s not a dark brown as you would recommend for the first pair but looks dark enough?

Monty

Would a dark brown suede derby work with tropical wool trouser?

Michael

Simon, I am considering getting the Edward Green Westminter, double monk, done up in a dark oak. Would you say that this dark enough to be versatile as a 5th shoe? Would you go the 82 or 202 last? When you say brown works with most suits in the office, I presume you mean everything except grey?

Michael

Simon, most grateful as always. One last question to pick your brain, if I may. Swinging off on a completely different tangent, for work suit purposes (mainly), which of the two dovers would you go?
https://www.edwardgreen.com/shop/dover-mink-suede-brown-202-last.html – the ones you own, and I have seen the many ways you have worn them to great effect, but largely more casual instances, or the:
https://www.edwardgreen.com/shop/dover-espresso-suede-espresso-606-last.html
Espresso, which is a darker brown (playing on your comment above with the darker being more work appropriate), and a more square last, and of course, a double leather soul (too chunky?).

Michael

Noted – and when they specify espresso being darker but cooler, that also places lower in the priority? To me cooler implies more formality – white (cool) vs pink (warm).

Gio

Hi Simon,

I found this useful article about basics for a shoe collection.

I have a huge collection of brown shoes in calf and suede: oxfords, derbies, monks, boots, loafers and so on.

However I only have a pair of black shoes for formal ocasions which is obviously an oxford.

I would like to include a second pair in black just to add some variety to my collection.

What do you recommend as a second pair in black? I rarely wear a suit. I’m thinking about wearing this new black pair with grey troussers (flannels and fresco).

Finally, one more question: any idea to wear black shoes apart from the grey troussers that I mention? I usually cind brown is better in my outfits, that’s why ask for ideas to wear black shoes in casual ocasions.

Thank you and best regards,

Benn

If a have a snuff suede chukka and a brown calf tassel loafer, would a snuff suede tassel loafer be too redundant? If so would you recommend either a different color suede (polo maybe) or a different style, or both? (I’m a big fan of snuff suede).

Benn

Thanks. I like the high vamped black loafer you list (with no tassels). Would a loafer like that in Polo suede be good, or do you think darker?

Benn

Is dark suede appropriate for year round wear?

Benn

And would the go with off white denim?

Jack

Hi Simon, do you think beechnut brown oxford/derby can be versatile?

Many thanks,
Jack

Jack

Interesting, it’s good that I have asked. I thought dark colours such as charcoal or navy would work better. I never thought of paler colour. Many thanks, Simon.

Jack

Hi Simon, I remember you liked tassel loafers from reading ‘How great things age’. Still, could I ask whether penny suede loafers fit into #3? Would penny suede loafers be too smart and less versatile if I mostly wear scales 4-5, 5-6, 6-7 based on your article, ‘Seven levels of formality’?

Many thanks,
Jack

Jack

Thanks, Simon.

Could I ask if you have noticed any fit difference between EG’s Belgravia and Piccadilly?

I believe I have flat feet (fallen arches, most of my shoes’ shape get easily deformed with the arches). I heard Belgravia has less support than Piccadilly but it would be great if you could share your thought about this.

Jack

Thanks, do you believe narrower shapes of the shoes would look better generally? In other words, would you recommend standard E fitting rather than F fitting if E fitting is bearable?

Jack

Hi Simon, do you think dark oak oxford could fit into number 2? or should I consider dark brown and dark oak in different categories

Many thanks,
Jack

Jack

Okay, so I assume dark oak isn’t versatile as dark brown.

Which colour trousers would be definitely ‘no, no’ for the dark oak shoes?

MBB355

If only someone would write a “Menswear Rules and How to Break Them” article about this :p

Jack

I have noticed Edward Green doesn’t offer dark brown leather. Does that mean Edward Green does not offer a pair of dark brown shoes that would fit under your category?

Many thanks,
Jack

Ian A

Surely the mink suede Chelsea Oxford from their range would fit the need for a dark brown shoe. Considering that any other colour than black would already be less formal in any case.

Jack

Oh, that is pretty odd. Which shoe brands would you recommend for dark brown leather oxford/derby?

Mark

How is delapre different to normal calf? It looks quite similar to cordovan

Carl

I am seriously considering getting Delapre loafers from EG. How do you find them?

Carl

Delapre looks fairly plain, to be honest. Utah must be superb, yet they no longer offer one. Do you think their dark brown delapre will look good if I wear them with charcoal and dark brown flannels?

Carl

Great suggestion, I shall try, thanks. Do you think the texture of the leather would pair well with smart denim? E.g. dark indigo and washed out black jeans

CARL

Simon I had a chance to try on the Piccadilly in dark brown Delapre and they were great as expected. My only concern was that they might be too similar in colour to what I have already, the C&J Harvard in dark brown, which held me back from getting them, although they are different in terms of style, leather and make. What’s your thought?

Alberto

Simon, if you had two business suits (grey and navy – soft shoulder) and wanted to buy one pair of shoes that works with both (and ideally with some jeans as well), knowing that dress code at the office is business casual, what shoe would you pick from the list?

alberto

Thanks, Simon. I was thinking of a black loafer such as Cheaney’s Hudson or C&J’s Boston as an alternative to a black oxford to dress down both grey and navy suits. Would you have any other suggestions in the same style and price ballpark? Thank you very much.

Benn

I have the top five (brown calf loafer in lieu of black) plus burgundy wingtips. I’m looking to add #7. Based on your post about the color black (which caught my attention) and also considering how current sensibilities lean more towards trousers and jackets (of all kinds, e.g., blazer, m65, safari) over worsted business suits, would you recommend the black loafer or something like a brown grained split toe derby?

I first thought your black loafer recommendation odd, but the more I thought about it it made great sense. My black cap toe oxfords see such little use these days that a black loafer could be a nice way to add some black into the rotation. And still not look out of sorts with a worsted suit. But then again brown split toes are also surprisingly versatile and grain leather brings nice texture.

Benn

Thanks – it would predominantly be chinos (khaki, olive, gray, navy) with a smart shirt and a jacket as a layering piece (French chore coat, cardigan, leather, m-65, soft tailoring). The rest of the time (maybe one out of five) would be gray fresco, or gaberdine.

Benn

Thanks for the vote of confidence. I’ll do just that – the dark brown suede loafers you suggested were one of the best purchases I’ve made – thank you!

Benn

My shirts are often something along the lines of an OCBD – to clarify

ayush

Simon!
Would dark brown suede derby instead of suede loafers look good with polo t shirt and chinos?

DrBruno

Very helpful article. Question: Can the brown suede loafer as shown above be worn in the summer or is it more of a fall shoe? What about a dark brown suede Oxford or Derby?

DrBruno

Great thanks. And if a shoe has a thin rubber city sole versus a leather sole, does that affect the seasonability?Lastly, I’m torn between a dark brown suede oxford or derby. Is one more versatile that the other? In particular, can they both be worn with smart trousers and casually with jeans?

DrBruno

Thanks Simon. I looked at your write up on ‘a sliding scale of formality.’ It’s really good and helpful, but I’m still trying to work this out.

Regarding formality:

Can a brown suede oxford be worn within the range of a suit (flannel) to a smart cotton trouser?

What is the range of a brown suede derby – a smart wool trouser to jeans?

Brian Beall

Dear Simon,
I love the look of a whole cut shoe and was wondering if it was appropriate to wear them with something other than formal wear which I never wear. What if I got myself a pair in a lighter color and wore them with a sport coat? Or even something more casual?
Thx,
BB

Ian A

How about having a look at Crown Northampton! They sell a Wholecut Sneaker called “the Upton” that looks great with casual wear while still obviously being a sneaker.

Oliver Zabar

Hi,
Late to the thread. What are your thoughts on a shoe such as the Edward Green Dover or the Crocket and Jones Hackett. Do you think these style of shoes can be dressed up, with a suit, and dressed down with jeans and a nice shirt or blazer. I love the style of these and find them quite easy to wear in all scenarios. Love the site and your reviews.
Best,
Oliver.

Oliver Zabar

Thank you for clarifying Simon!

Jackson

Hi Simon

What’s your view on paraboot as a brand more broadly? In terms of quality and overall output?

I’ve come to really like them and think they are a wonderful addition to a smart casual wardrobe, especially if there’s a touch of Ivy in there. Got a pair of split toe derbies with a leather sole without the green tag and think they work rather well with relaxed tailoring too.

I’ve got the itch I get whenver I begin to like a particular maker, which is that I want to stock up on almost everything they produce and some of their workboots look pretty lovely to me.

Jackson

Doesn’t surprise me that you feel that way about the aesthetic! In fact, I rather anticipated you’d say that both about the value and the style aha

The Michael is perhaps a step too far for me. I find some of their boots, like the vien, to be quite good looking. The chambord and the avignon that drakes put out with leather soles recently I thought were fantastic. I prefer the avignon split toe derby superior in pretty much every way to the split toe st crispins I got some time ago

Stephan

Dear Simon,
How would you wear a relatively slim brown blucher? Do you think it could be pulled of with woolen suits, or at least tailored trouser + jacket combos? I work in an office, but am often out and about and walking to the metro, so something that is good for the elements and can pair with tailored clothes during the colder/damper months. This is a pair I’ve seen recently, from Ludwig Reiter:comment image. Thanks,
Stephan

Jack

Hi Simon, I was wondering what you think of C&J’s loafer Boston last with a semi-formal outfit. Would you say it’s too wide/rounded to go with tailoring like Alden’s Van last?

Many thanks,
Jack

Jack

Thanks, Simon. It is pretty difficult for me to choose a brown suede loafer.

To be honest, I would like to get EG’s Piccadily as they look beautiful to me, but I have flat and wide feet, and I feel like my feet are in a pencil sharpener if I exaggerate. Also, Piccadilly’s original last shape disappears by my wide feet.

On the other hand, CJ’s Boston feels comfortable, almost like wearing Common Project sneakers. Still, I agree with you that this looks relatively wide, especially since most of my trousers are (18cm-18.5cm).

What would you suggest at this point?

Jack

Hi Simon, I was wondering what you think of dying the suede shoes. For instance, taupe to dark brown?

Many thanks,
Jack

Martins

Since you cant strip suede, end colour will be mix between what colour shoe currently have and what dye you use. So like Simon says, if you wont be upset if it doesnt work, go for it. I managed to dye two pairs in a nice colour, but it wasnt what i had in mind so took a while to get used to end result…

Jack

Hi Simon, I am considering investing in two oxford shoes, in black and dark brown. Due limited budget, I am considering choosing one from the top-end maker and the other from a mid-range maker. I always thought ‘black oxford’ was a must and essential for men and therefore thought I should invest more pennies in the black.
However, I mostly wear separate outfits and only wear suits around two to three times yearly. In this case, would you invest more in the dark brown cap-toe if it were you? Would black cap toe be too formal/smart for the separate outfit?

Many thanks,
Jack 

Jack

Thanks, Simon.

Jack

Hi Simon, I have been searching for the dark brown oxford, which could fall under the number two but I couldn’t find one as Edward Green’s dark oak was crossed out due to versatility. Would you have any RTW makers or models to suggest at a similar level with EG?

Many thanks,
Jack

Jack

Thanks, Simon, for your suggestions.

Personally, I find G&G and Stefano Bemer’s lasts too narrow and slightly showy for me. Also, I think G&G’s dark brown isn’t dark enough. I do like John Lobb’s styles, but their prices aren’t very convincing to me.

I found C&J hand-grade collection’s Audley in a dark brown, which seems dark enough and versatile, but given that I am looking for a similar level as EG, do you think it may not be the best option for the long term? I have been browsing for the right pair of dark brown oxford for so long, but many brands seem to use ‘mid-oak brown’.

Jack

Okay. If I mostly wear trousers in mid-grey, beige, olive, and charcoal, do you think the EG’s dark oak may be useful as the dark brown shoes, and maybe wear the rest of the other colour trousers such as charcoal or navy with black shoes?

Jack

Sorry, charcoal should not have been included in the first list.
Many thanks, Simon.

Markus

Dear Simon,
Thank you for this great article. I have one question: When you live in an area, where snow / slush and ice is quite common (plus the accompanying salt and anti-slip gravel on the streets) like I do and walk a lot, what shoes do you recommend for a business casual look also working for casual.
Would a Vibram-like sole on e.g. a dark-brown brogued derby work in your opinion?
Thank you and kind regards
Markus

Markus

Thank you. Very helpful.

Stefan

Chukka boots in dark brown suede is my favourite. I have had my carmina for 6-7 years now, and unfortunately they have not last as good as my other shoes from crockett for example. If I would like to make an upgrade when I replace my chukkas, where should I look? Very thankful if you could give some recommendations.

Stefan

Of course, that would be the given choice for me, I was just wondering if you thought it would be worth spend some more money on a pair of edward greens for example. I don’t know about suede, but for me those shoes have been worn out the fastest even if I have taken care of them. So I suppose it’s a good idea to spend som more money to get best quality possibly.

Vineet Jain

Dear Simon,

This is another immensely helpful post. I have been a reader of your blog from last few months and I discovered it when I intentionally started to find my style. I’m in early 30s now, and have finally understood the importance of uniform for me. I spent most of my 20s trying out all kind of outfits, partially because I had this idea that style meant having ability to wear a broad spectrum of outfits. In the hindsight, I would classify that phase as costume rehearsal which eventually proved useful in finding my style. Anyway, I digress. My question was about capsule shoe wardrobe.

Before I ask advice, let me share three outfits I typically wear.
1. Everyday – dark jeans, white shirt, and black knit/jacket.
2. Semi formal – grey wool slacks, white shirt, and navy blazer.
3. Formal – white shirt, tie, navy suit.

Coming to shoes, I don’t think I have started to appreciate loafers yet because I like my feet to be gently held by laced shoes. I have dark brown suede derby, and dark brown grain derby both in casual lasts, a color 8 shell shoes derby in smart last, and a black calf cap toe Oxford. I’m craving for a boot, and considering a snuff suede boots (probably not chukka, because I like the high boots more). While I do understand it’s a process to understand what suits one, but buying shoes is fun and I would not like to end up owning two dozen pairs of shoes. Could you please suggest if you see any essential gaps in my shoe wardrobe, after all, I do want to look sartorially apt.

I would value your advice highly.

Sincerely, V

Vineet Jain

Thank you Simon. I’m going to look for a good dark boots, and perhaps, soon try a pair of loafers as well. Like you, I find dark brown suede very versatile and also most beautiful color.

Joseph Sanger

Thoughts on John Lobb? I see them missing from most conversations

Joseph Sanger

Wow that was a quick response, thank you! Yes you’re right, referring to Paris RTW. I was given two pairs and immediately went here so I could read if I’m allowed to love them or not lol, was surprised to see almost nothing.

Jack

Could I ask what your thought is on the John Lobb Paris dark brown museum calf? Do you think it could be a versatile dark brown and it could age well?

Many thanks,
Jack

Tom Rainsworth

I splashed out on a pair of C&J Harvard in dark brown cordovan and use them so much I’d like to invest in a second pair of loafers. I mostly dress in the “casual chic” end – nice knitwear and smart chinos. Occasionally jackets and wool trousers, where cold colours are preferred. It will be Belgravias next but I cannot decide between black calf and dark oak. What would you advise Simon?

Jack

Hi Simon, do you think Edward Green’s Cardogan dark oak can be versatile? Or would you suggest more subtle models such as Chelsea or Berkeley?

Many thanks,
Jack

Chris

Simon, Of all your non-workwear boots – (Alden’s jumper, EG Cranleigh, EG Galway) which one gets the most use and why? Is any of them a stand-out “favourite” for you like your Belgravia loafers are?

Jack

Hi Simon, do you think the loafers from the link below could be worn for more formal occasions than the black penny loafers? I am not entirely sure whether that design could be useful for formal occasions.

https://www.johnlobb.com/en_us/sales-uk/upton-prestige-sole-17407#selection.color=Black%20Oxford%20Calf

Many thank,
Jack

Aaron

I already have a pair of black captoe Oxfords, black half brogued Oxfords, brown plain toe Derbys. I wear a suit every day for work, although in an office I’ve definitely seen people wearing black boots. If I were to buy a pair of Chelsea boots would you say a black pair would fit into that rotation? I’m trying to decide between that or some more rounded, brown ones to go with jeans and chinos.

Mateusz

Hi Simon
What shoes would you suggest for someone who can’t possibly find loafers that fit? I mean mostly on the casual chic side of things. My most-worn shoes are a pair of chukkas in dark-brown suede, but they’re not really an option for summer.
I’m thinking of a brown suede derby, but it gives me cold-weather associations. Perhaps in lighter brown? Monks seem a bit too showy, espadrilles (laced in my case) are fine but s)can be too casual. Any suggestions?
A second question, inspired by your double-brown post, do you think black derbys (the sleek and modern veariety rather than the chunky countryside one) would work in that kind of look, or are they better reserved for tailoring?

Kris

Simon, what about a Norwegian split toe derby (possibly in suede)?

Benn

Simon, for either the brown suede or black loafer – your thoughts Danite and it’s impact on the formality of the shoe? Not a double sole with Danite – still slim. But would doing so limit the ability to wear say the suede with blazers formals shirts and ties? Thank you!

Benn

Thanks, as always!

Mark

Hi Simon, thank you so much for this article. I am curious whether you feel derby or Oxford cap toe shoes would look more appropriate with a suit but no tie look (with a button down for a shirt). Im leaning towards the derby… but I was really hoping you could elucidate!

MK

Thank you for this informative article! If I were to pick a calf penny loafer, what would you say to choose between museum calf or regular calf? Is there anything wrong with the combination of museum and penny loafers?

Ashish Tibrewal

Hi Simon. I recently discovered your website and have loved reading through it. Thanks for sharing your tips and guide to (tailoring) style and fashion.

My question to you is what are your thoughts on Crown Northamptons? I was looking to get the following pairs:

1. HARLESTONE HAND STITCH DERBY – OFF WHITE VEG TAN CALF LEATHER (https://crownnorthampton.com/collections/bestsellers/products/harlestone-hand-stitch-derby-off-white-finest-calf-leather)

2. WOODFORD DESERT BOOT – SAND KUDU SUEDE (https://crownnorthampton.com/collections/stitchdown-construction/products/woodford-desert-boot-sand-kudu-suede)

It would be really helpful if you could look through these and share some suggestions. Thanks once again! 🙂

Lamschke

Dear Simon,

what is you opinion about a mahagony/chili or even oxblood quarter brogue?
Is it versatile enough to wear it with suits and combinations?

Have a nice week.

Angus

Hi Simon, some of your responses to earlier queries have touched on this but I hope you don’t mind my confirming.

I was wondering how you think a dark brown suede derby like the EG Dover or C&J Hardwick might fit into this collection? I was thinking about adding one of these – probably the C&J Hardwick, for budgetary reasons – to my collection, but your article has made me wonder if I should instead be adding a dark brown suede chukka.

It seemed to me that both styles could perform a similar role smart or business casual role, but that the EG Dover or C&J Hardwick would be a touch smarter and therefore elevate an outfit just a little bit?

I work in an office environment which is very smart for meetings etc (dark suit and tie, black oxfords) but otherwise fairly casual – jeans or chinos with an oxford shirt, for example, is fine, but so too would be something a bit more formal, like flannels with a jacket. I am looking for something that works both in this office environment and on weekends.

Thank you for this, and all your excellent content.

Angus

Many thanks Simon.

Another question if you don’t mind. Looking at dark brown oxfords, how would you assess the quality of the Stefano Bemer Essenziale collection pictured in this article, against a mid-range Northampton brand such as C&J? The Essenziale collection is a step up in price from the C&J Main Collection and roughly comparable to the C&J Handgrade Collection, so I was wondering if you thought that properly reflected their quality?

Also, I notice that in your article about bespoke shoes you mention that you have found mid-brown to be the most useful colour. Would you now recommend mid rather than dark brown oxfords for a capsule collection?

ayush

Hi Simon! Do you think slim dark brown penny loafers in leather look good with dark denim? I particularly like the combination so much when i am wearing a casual shirt and some nice dark denim and so wanted to get your opinion on whether would it be a nice combination.

ayush

Understood!
Is there any chance of dark slim suede loafers also being smart enough for ready to wear chinos and dark denim or do you find it appropriate?

ayush

Could yo advice whether the brown suede tassel loafer shown in the article in the third picture wearable with a ‘polo and chinos’ and a ‘shirt and jeans combination’?

Christos

Hi Simon,
you are mentioning dark olive as a second pair of chukka boots. How would you combine them? It seems rather difficult to me, can’t think of a combination that’s striking.
Further down in comments section you write that green coloured shoes (I suppose that dark olive goes under green too?) are rather difficult for combinations that match and that the rest of the outfit has to work around those shoes.
Many thanks in advance!

Reid Stapleton

It’s not 5 shoes but my picks would be:
Black leather, burgundy leather, & brown nubuck plain toe Derbys
Elastic in step/side gusset slip ons in same three colors
Reddish brown/oxblood Moc Toe Venetian Loafers
Black 5 eyelet Cap Toe Oxfords.
Not included but also would like are derby laced plain toe boots and casual shoes such as gym sneakers, LL Bean style Blucher mocs and espadrilles.

AA

Agree on the suede loafer being the most useful shoe. I would , however, add that a dark navy suede loafer is as useful as a dark brown one….

AA

Sure, to each his own. It largely depends on one’s complexion. For the “summer” and “winter” types, shose skin is flattered by colder tones rather than warm ones, the navy suede loafer is practical. Yes, it does not provide much contrast to dark indigo denim, but it compliments all the other practical pant colors (grey, mid blue, cream/off white). The suede texture itself is what provides the desired degree of contrast to any fabric above

Rob

Greetings Simon, i keep returning to this thread!

I know you have a pair of unlined EG Dovers – i am sorely tempted by these as they seem extremely versatile. I was wondering whether you think they are suitable for workwear i.e. chinos/jeans and a sweatshirt? I rarely wear anything more formal than flannels, and my sports jackets are casual in fabric/cut. It seems that the Dovers may pair with most of my wardrobe, and was wondering on the range of outfits you have worn them with.

Sincere thanks.

Rob

Many thanks Simon. Do you find this an issue with your Cranleigh boots? They are also on the 202 last, so should be equally slim?

Good idea to try in store – the cost of EGs now makes me too nervous to buy them without throughly trying them in store.

Andrew

Hi Simon,

I’m working on building my shoe collection, and am about to begin saving for my next shoe purchase.

My office isn’t that smart, so I don’t wear suits to work. Rather, something like the “casual chic” look is what I’m aiming toward. I already have a pair of brown suede loafers, a pair of brown suede chukkas, a pair of tan loafers, and a pair of Alden full strap color 8 cordovan loafers.

Therefore, I’m thinking my next shoe purchase would be a darker brown, non-suede loafer. I’m finding that I love the look of cordovan, as to me, it has a much more subtle and interesting look than regular leather. I’m inclined, therefore, to make my next purchase the Crockett & Jones Harvard loafer in dark brown cordovan (as opposed to getting a loafer in dark brown calf leather).

Given the casual feel of my office (where oxfords and derbies aren’t really needed), and given what I already own, I *think* the C&J Harvard as a next purchase makes sense for my situation. But I’m wondering if there’s anything I may not be considering that I should. In other words, is there a strong argument that, in fact, a loafer in dark brown calf (rather than dark brown cordovan) would be a better next purchase?

Thank you for your help, Simon. It’s through Permanent Style that I’ve been introduced to a whole new sartorial world.

Jack Anapes

Simon,

Apologies if this question is misplaced. I am soon to be married and in the process of putting together an outfit. I plan to wear a mid-grey SB suit with peak lapels and a DB waistcoat. With versatility in mind, I am thinking about dark brown oxfords from Crockett & Jones (“C&J”). While I am open to other makes/brands, to my untrained eye, they appear to be solid, well-made shoes and perhaps a gateway to footwear nirvana and/or bespoke bliss but I digress. With the wedding date nearing, C&J do seem to tick the boxes (for me anyway) for value, convenience, and budget. 

In trying to strike a balance between an appropriately smart shoe (simple, sleek, and clean) for a wedding and something a bit less formal but more versatile (via texture, pattern, colour, etc.), I would love your thoughts and opinions on the following:

Style: Do you think a dark brown wholecut Oxford with a light medallion design would work (e.g. C&J Weymouth 2: https://www.crockettandjones.com/collections/mens-oxfords-collection/products/weymouth-2-darkbrown-calf) or perhaps a dark brown adelaide or cap toe Oxford with or without light broguing?
Quality: Realising there may be diminishing marginal returns, do you find C&J “hand grade” to be worth the additional expense or would you suggest putting the additional money towards an “upgrade” to another brand?
Sole: Is a (low profile) rubber sole ever appropriate for a more formal event or is leather always the better choice?
Lasts: If any, which C&J last do you like/prefer?

Of course, feel free to ruthlessly edit and apologies if this has already been addressed elsewhere on PS. Further, please feel free to simply say I’m asking too much of a single pair of shoes. After all, a one-size-fits-all approach often leads to master-of-none type results.

Many thanks as always

Jack Anapes

Simon,
Thank you for your speedy and thoughtful advice. I am (or at least was in light of your comments) considering the C&J Weymouth 2 dark brown Oxfords which are built upon last no. 373. Admittedly, however, I am a “newbie” and know very little about lasts (or shoes and other sartorial affairs for that matter). I was initially drawn to the shoe simply because it seemed to have a more slender, elongated, and chiseled toe shape which in my mind, suggested a more elegant and thus smart shoe. I thought dark brown would be more versatile than black and the smooth, uninterrupted (wholecut) surface would compensate for any “smartness” lost by opting for the dark brown as opposed to black. The medallion toe, I thought added some visual interest and takes the edge off of the more formal wholecut form. That’s what I tell myself anyway but truth be told, I kind of liked the zing – if not, bling – of the medaillion toe as well. Plain oxfords, while sleek and smart, can appear to be well…just a bit plain to me. Heresy aside, upon considering your comments and further reflection, I now “know that I know nothing” and really must strive to be a bit more subtle and reserved – especially given the party that is going on above the shoes as you noted. Your thoughts and comments are truly appreciated. I will look for a dark brown or black plain cap toe or Adelaide Oxford as suggested. Any suggestions regarding brands/makes at the C&J hand grade level or similar price point and available in London would be greatly appreciated.

Many thanks,
Jack

Jack Anapes

Simon,
As always, thank you for the helpful information and guidance.

Jack

Hi Simon, I am considering buying a pair of EG Piccadilly, but I am unsure whether I should go half-size up. If I wear my usual size, I feel pretty snug around my insteps and a slight pressure around my little toes, but otherwise, they hold my feet very well. But I don’t feel any snugness around the vamp and little toes when I wear a half size up from my usual size. They are very comfortable, but I am concerned whether the shoes would hold my feet when they stretch over time (they are suede). I remember you mentioned that you would start buying half-size up for your loafers, and I was wondering whether you also feel this would work for me?

Many thanks,
Jack

Jack

I see. Thanks, Simon.

When you say pressure, do you mean one from objects such as shoe stretchers other than my feet? Because if I go for my usual size, I feel some pressure on my feet from the shoes, so there must be some pressure applied to the shoes against my feet as well. A sales associate who has seen me wearing them suggested not to go up a half size as he believed the loafers must be pretty snug in the beginning to hold the feet well in the future when they stretch out, and from my experience, this is a typical suggestion from shoe brands for loafers as you may be already aware. But I couldn’t make a decision there hoping they will stretch out to the point where I feel comfortable.

I was wondering if you also had some heel slips when you went up a half size. If so, did they go away/reduce when the soles broke in? Sorry, even though I am aware we would have a different fit as our feet are different, I often find asking for your experience or advice helps me make a better decision.

Jack

I get what you are saying. Thank you once again, Simon.

Benn

Simon, where would you say a a dark brown calf split toe derby would fall? Could it sub out the dark brown Oxford? Or would it be closer to the grain derby mentioned? They seem increasingly versatile.

Cormac Lynch

Dear Simon,
Another fantastic thread. It seems shoes are one of the toughest category to build wardrobe for, as there are so many elements, such as color, type of leather, last shape, style of shoe, thickness of soul, etc. I love your picks which fit well for a typical PS reader, with jacket-odd trousers heavy wardrobe.

I would certainly say for people not wearing jackets, almost none of the time, could also add a pair of tennis shoes, like your Doek’s or Common Projects (to pair with workwear Chinos), along with oxfords, loafers, and boots/derbies. I personally tend to get a lot of wear from my dark brown derbies, and tennis shoes, as I’m in Jeans or Chinos most of the time. Loafers are quite useful too, as they smarten up my typical outfit instantly and go seamlessly with more formal trousers as well.

To me, most under used shoes in my wardrobe are a pair of black calf Chelsea (zip) boots in a quite smart last. Every time I wear them with Jeans, they get a lot of attention, due to their association with Saint Laurent/Celine aesthetic, which I heavily despise. Would you know of ways to style them while taking focus away from them?

Cormac Lynch

Thank you, Simon.

For people like me, who live on West Coast or wear elevated workwear, such an article can be incredibly useful. I did learn quite a lot from your weekend wear articles. Having said that, I reckon your typical reader might be in tailoring most of the time, yet they might find a great value in understanding style elements of away from work outfits.

And, thanks for the advice on boots. I guess, why not try embracing the aesthetic before completing shutting it out.

Have a wonderful week!

Peter Hall

Do you think a pair of slim charcoal chinos would work here instead of jeans? Just a touch smarter?

Peter Hall

oh sorry.Not very clear. Just responding to Cormac and his Chelsea boots.

Cormac Lynch

@Peter, I reckon, yes, these smart boots might go well with darker pants/chinos. Lesser contrast might help to keep the outfit subdued, even if it’s smarter. I would try that. Thank you.

Cormac Lynch

Dear Simon,

Hope you have been well.

Few weeks back I had requested advice on capsule shoe wardrobe for people who don’t wear suits or jackets. I found this post from Put this on to have some good advice, which is equivalent of taking less smart shoes from your list here and adding a few casual ones. But it would be great to hear your thoughts, when you find appropriate time.

Have a wonderful week ahead!

Martins

I suspect i know the answer but ill ask anyway!

I have a pair of trickers stow boots in a strange dark brown leather (strange because noone can identify the leather). Commando sole, storm welt.
Love them with jeans but they are not good with any remotely smart trousers.

The only hole in my shoe collection is dark brown suede.

Today i saw trickers wingtip derbies with a slimmer (but still quite chunky) welt, single leather sole in a really nice dark brown suede! Best of all, 50% off. I do like them but my concern is ill end up wearing them just as i do stows. Jeans, and one pair of 8 wale drapy cut ghurka sand corduroy trousers. I want something a tad more versatile! At least to go with caramel and olive corduroy and ralph lauren/hackett chinos without it being “a look”.

https://trickers.com/collections/bourton-country-shoes/products/bourton-country-shoe-lightweight-cafe-repello-suede

Martins

Yes and thank you!

Smith

I have been gifted a pair of C&J Tassel loafers in navy, what outfits / combinations can I style them with ? I dress casual and sometimes smart casual.

Cheers,
Smith

Peter Hall

Just to echo what Simon has said Mith,I have a pair of navy deck shoe so even more casual, and the only pair them with cream or white jeans (plus blue and white Oxford). They get lots of summer use, but that’s about it.

Smith

Yes, they are an odd one. But the person gifting me reasoned all the shoes I have are brown or black 🙂 Could not find much recommendations on other forums / YouTube too.

Thanks,
Smith

SamS

Definitely a thoughtful gift, even if it might be a tad misguided in the choice of color. Navy shoes (at least in leather) will always be a bit odd in the context of classic menswear, since there’s little tradition of wearing navy leather shoes.

I think Peter Hall is on to something: ecru jeans. Embrace the fact that loafers were traditionally fairly casual shoes, and wear them in a casual chic way: ecru jeans (or maybe white linnen trousers) and a navy knit, either a polo or a crew neck. I think wearing something else in navy would make the odd color stand out less. Definitely a leisure look more than an office look, though. I can imagine it would not work as well in the office.

Peter Hall

Do you think PS could look at the sailing influence in casual wear future Simon. You see plenty of stripes,etc in our style nowadays.
I think the faded reds and blues of Ivy are derived from this,but a sensible investigation would be interesting.

Stephan

Can I just jump off-topic here say here that I loved this case of “to borrow from Peter to pay Paul”, or as I heard it once “to unclothe Peter to clothe Paul” in this comment by Simon 😀

Jonathan

Hi Simon,

This is very useful article and one that I keep coming back to.

I just had a query on the loafers – I’m not a big fan of loafers (It’s purely a personal preference, and I make no judgement about yours or anyone else’s style) but could do with a shoe that fits the brown suede loafer spot, that bridges smart and casual.

I was wondering whether you think a brown suede lace up, either a derby or a brogue (with heavy broguing) would more or less do a similar job? Probably a bit less versatile no doubt, and I accept will be warmer in summer with less of the foot exposed, but I am just pondering where to put my money. Any advice will be greatly appreciated!

Jonathan

Great, thank you! Edward Green is still a bit out of my reach, more’s the pity, but I shall start having a look around.

Colin

Hi Simon – I am debating between three colors (mink, raw umber, and mole suede) of the EG Banbury chukka boot. I know that mink suede (the dark brown color) is the most versatile, but is there a reason I might choose one of the other two instead for a first pair?

For context, I’d like the boots to pull double duty between work and weekend. At work, I wear wool trousers (flannel and high twist in light/mid grey and tan) and dress shirts with no jacket. On the weekends, I wear jeans in light/mid blue and off white and chinos in lighter colors.

My gut says that the lighter colors might pair better with many of the lighter colored trousers I tend to wear, although the dark brown suede certainly goes with those too.

The only other hesitation I have in ordering the mink suede is that I plan to order a pair of Dovers also in the same color and I already have a pair of loafers in dark brown suede. Both the Dovers and loafers are for the office.

So, does it make sense to have some variety in the colors of my smart-ish shoes, assuming that I am trying to build a capsule as this article discusses?

Many thanks!

Colin

Hi Simon – I ended up getting the Banbury in mink suede. Thanks for the advice.

I’ve been looking for a pair of Dovers on the 202 last in mink suede (the lined version, not the unlined version), but I cannot find them. However, I have found one stockist that has them in espresso suede.

Is the espresso suede close enough to the mink suede to not make a difference? I generally prefer warmer/richer browns and am worried that the espresso suede will be too cold/bitter, meaning it might not pair as well with warmer colors of trousers (e.g., tans, light browns) or jeans and chinos if I were dressing them down.

What is your opinion on the espresso suede? Should I just use the MTO program to get the mink suede, or is the espresso close enough to make the MTO surcharge unnecessary?

Thanks!

Mark

Hi Simon,

I need a new black cap toe Oxford because my current pair is the wrong size (acquired long ago before I knew a good fit). Hard to find my size in most shoe brands as I wear a narrow fit. 7C US or 6.5 D UK (EG or G&G). I don’t wear black caps much as I no longer go to an office but still need a good pair.

I would prefer the EG (82 last) or G&G (DG70 last) caliber of shoe but hesitant to spend that kind of money on a shoe I know I won’t wear much (strong preference for brown shoes and like the English makers though open to others). I would consider C&J but they don’t offer narrow widths for the most part.

Any recommendation?

Mark

Thanks, Simon. Yes, I have inquired with EG and they can do it. I believe a pair in a narrow fitting could be reserved in their current production since it is a stock shoe. Crockett also seems to have a special order department though in USD it is approaching the EG price level so would probably go with the EG if I stay in that range. I am looking to keep costs down on the black cap since it will have low utilization and to prioritize other EG models I know I will utilize much more like a brown leather or mink suede Piccadilly.

Anonymous

First, thank you for your valuable insights on your blog. These wardrobe building posts are very helpful!

You mention Dark Brown leather and Dark Brown suede in terms of versatility. Is Edward Green’s standard “mink suede” a dark enough brown based on what you are suggesting? They seem to offer darker brown suede (e.g., on the Shanklin), but only mink suede on the Belgravia and Piccadilly, etc.

For brown leather, their Chelsea Oxford is only offered ready to wear in Dark Oak, but that appears too light based on your writing and comments. Is there a darker brown calf leather that you recommend from Edward Green that could be used for a custom make? Or another shoe of theirs I could use as a comparison to the brown color you are suggesting? Thanks!

Anonymous

Besides the EG Belgravia or Piccadilly mentioned do you have other recommendations for a brown suede loafer? What about the C&J Cavendish or Alden suede tassel?

John

I recently stumbled upon a pair of handmade, black, whole-cut oxfords; however, they are pebble leather, so the formality gap is odd. Would you say that that makes them too informal as a replacement for [smooth calf] cap-toe oxfords with a more formal suit or even black-tie?

John

Hi Simon,
Can a pair of cordovan loafer be worn in warmer weather, for example with linen trousers in spring and summer, or is it only appropriate in cooler weather?
Thanks

Anonymous

Is the Alden LHS in dark brown a good option for #3 above or are they not dressy enough? I am look for a brown suede loafer that can be worn with gray trousers (flannel or fresco) and a navy blazer or sports jacket, but also be worn with chinos. If not, would the Alden brown tassel version or C&J Cavendish work instead?

Emil

Hello Simon and lovely subscribers! If I were to live and study in Edinburgh for a year, what would be the 5 pairs of shoes/boots/trainers you recommend I bring? I wear Classic Menswear, Ivy, and visvim/Real Mccoys/Engineered Garments aesthetics. Thanks!

Some options in my current wardrobe:

Alden 975 longwing cordovan
Alden NST snuff suede
Alden Indy boot mid brown
Visvim grizzly boot dark brown with denim blue
Visvim two engineer boots damaged mid brown
Visvim brigadier suede camel
Crockett and jones suede tassel loafers dark brown
Crockett and Jones unlined shell cordovan penny loafer dark brown

Emil

Thank you for the prompt response, Simon. I currently live in Manila where it is perpetually hot and humid. I heard that Edinburgh weather is cold, rainy and windy. Firstly, should I avoid suede? Secondly, wear more boots or Gore Tex trainers which are rain-appropriate? Am I missing something?

Emil

Thanks Simon. That’s great to know! No need for Gore Tex then. Also, I find Dainite / city soles quite slippery on wet surfaces. Do you have the same observation? I could rather opt for other types of shoes with better grip if this would be the case. Any remedy for Dainite soles to grip wet surfaces better?

Emil

Thanks Simon! Will bring my cordovan and suede shoes, as I’ve read in your helpful articles. Hope to bump into you in London, Scotland, or anywhere in the UK. 😊 Cheers!

Jack

Hi Simon, I am considering to invest in a pair or two of new shoes to add to my shoe collection and it would really help to get some advice from you before I make any purchases.

I currently have a shoe collection of:

EG Piccadilly Mink suede
C&J Harvard in dark brown cordovan
C&J Boston in dark brown suede
C&J Chukka boots in dark brown suede
JL Lopez in dark brown suede
JL Lopez in black calf leather
Alden LHS in snuff suede
EG Chelsea in black calf

As you may have noticed most of my shoes are loafers, especially in dark brown suede and clearly I rarely need very formal shoes such as oxfords. I mostly wear an odd jacket and trousers. If it were you what would you go for the next pair of shoes?

Many thanks,
Jack

Jack

To be honest, I am a bit bored of wearing loafers (especially in suede) although they’ve been very useful and I have enjoyed wearing them as they give a relaxed look. I think it would be nice if I could have a pair that could add a slight variations to go nicely with a pair of flannel trousers and a tweed jacket.

Jack

That’s an interesting suggestion. I’ve always wanted to add in black suede in loafers but wasn’t quite sure how usefully I could use them.

I was thinking of changing the style and material, for which the derby you’ve suggested could be a good choice. But would you say going for to calf leather in dark brown/oak would suddenly make my outfit look quite dressy compared to what I’ve been wearing?

Jack

Thank you very much for your advice, Simon. I think I would go for the black suede but in loafers as I can’t find any in derbies from the English makers.

Would it work if I wear them with a jacket in a warmer colour such as PS tweeds as long as the trousers are in a cold tone?

Jack

Hi Simon, following this question here, I am currently thinking of getting the EG Galway or SaintCrispin’s chukka boots in dark brown suede. The former will be a completely new style and the latter will be to replace my C&G chukka boots.

If I were to go for the Galway, I know the dark brown suede would be the safest choice for them to blend in easily with my outfits. But as I mentioned before, I have too many dark brown suede shoes in my collection. As one of the aims for my purchase is to give some variation, do you think the Galway in dark brown Utah or London grain leather could be as useful as the dark brown suede? For instance, if I want to wear them with jeans or officer chinos for the weekend, do you think they could go well?

Many thanks,
Jack

Jack

Thanks, Simon.

I have one more question.I’ve been struggling to decide whether I should go for a completely new style of boots, which in this case is the Galway in Utah leather, or replace/upgrade my C&G’s chukka boots in dark brown suede to Saint Crispin’s. I think I would eventually end up buying both of them but I would like to spread the purchase across this winter and next winter. I know this entirely a personal choice but what would you do if it were you?

Jack

Thank you, Simon.

After speaking to you, it sounds like the Galway boots could be as versatile as the Chukka boots if they could work with jeans and chinos. However, since you listed Chukka boots in the top 5 essential lists, could you elaborate on when you would found it easier to wear Chukka boots?

Benn

For the black calf loafers in your top five, what are your thoughts on tassel vs a sleek Penny when it comes to versatility? (I already have some brown calf Alden tassels that are fabulous).

Benn

That’s great advice to allow for either direction. Thank you.

David

Simon, is there an alternative to the brown suede chukka boot? Don’t get me wrong. I really like them, but they don’t like me. I have thin legs and long feet, and the uninterrupted expanse of the chukka does not do me any favors. Would a brown suede moc toe chukka be a suitable alternative?

David

Great. Thank you, Simon.

ANONYMOUS

Hello Simon, 

If you don’t mind can you share your thoughts on these quotes below?

“Your feet will sink into the shoes, and the heel slips will eventually go away”,
“Your feet will mould into the shoes, and they will feel comfortable soon”,
“The leather/suede will give much, so your discomforts will disappear.”

These seem to be popular terms used among sales associates of some of the shoemakers. Although they are not wrong, sadly, I have to say they are misleading and overused to convince the customers to some extent.

Zy

Simon, I am wondering how a black smooth calf leather penny loafer reads to you? More casual, or more formal?

I am wondering whether getting a grain loafer will be too in-between the two to truly be useful.

ZY

Essentially, I am looking for an Ivy style loafer than can be worn with a suit and jeans, if need be, other than brown suede. My instinct is black grain, but I am wondering whether smooth calf could do the trick, too, or whether it would be too stark a contrast with jeans and knitwear.

Alexander

Hi Simon, I really appreciate the detailed discussions that your posts garner. I have a pair of C&J Audley black oxfords (per this capsule collection) and appreciate your advice in the comments to add toe caps to extend the life of the leather sole. I have been agonising over which loafer to purchase that is both comfortable and versatile for both work and smart casual. I think from most of your comments it appears that the Allden Colour 8 Cordovan 986 is a great choice, but I just wanted come back to the query regarding leather/rubber soles. I am now living in London and assume that so long as I am rotating the shoes I wear, the leather sole is an appropriate choice and shouldn’t deteriorate too quickly, but isn’t a rubber sole better for longevity and more comfortable for walking between offices etc? I understand from your previous comments that this is more a matter of formal/informal, but would appreciate your thoughts again if you don’t mind. On a related note, on a more rainy/less drizzly day in London, what type of shoe would you recommend that crosses that work and smart casual criteria? Also as I continue to add to my shoe collection, would a brown suede loafer be appropriate for a smart casual and casual use? I’d appreciate your thoughts on tassels/no tassels, sole and style/brand if possible please. Thank you in advance!

Alexander

Thank you Simon. I guess it’s also a matter of what the manufacturer offers, with most brands focusing on leather soles. Do you have a preference comparing the Alden 986 and 684? Also on the more casual brown suede loafer, do you have any useful thoughts on whether tassels are necessary?

Alexander

Thanks again Simon, very helpful. Agree that the 684 is smarter but I am similarly wanting to ensure they are comfortable enough to be worn all day. I have wondered if I’m being boring for preferring no tassels, but I must admit that I do find them a bit showy.

Alexander

Agreed. I assume you still prefer the E&G Piccadilly when it comes to a penny loafer with no tassels? I think this is a tad out of my price range, but I think C&J do a similarly nice suede loafer (unless you have any other suggestions). Conscious that I am considering buying two loafers here, the Alden Colour 8 for work/smart casual and the brown suede for casual affairs. Do you think they are sufficiently different? I think the Colour 8 is my alternative to the brown oxford you have suggested in this article…

Alexander

Agreed. As far as the suede loafers are concerned, I assume you still prefer the EG Piccadilly? As this is a bit pricey for me, would the C&J loafers be a solid middle ground? I’m conscious of the fact that I am considering buying two sets of loafers, but I think the Colour 8 bridge the work/smart casual (in place of the brown oxfords/black loafer in this article) and the brown suede are the smart/casual shoe. Do you agree with this approach?

Andrew H

Hi Simon,

I’m trying to expand my shoe collection and was hoping to get your advice. I currently have two black cap toe oxford and one white sneaker. I work in finance so need to wear a suit for 4 days a week and business casual on Fridays.

I was going to get the EG Dark Brown Suede Picaddily Loafer, a chukka boot and perhaps 1 black calf loafer.

For the Chukka, I was looking at the EG Chale in dark brown, but I’m not sure if you’d recommend them. I’m also not sure if I should get the Chukka in same Dark brown as the penny loafer for versatility (dark brown is most versatile but should both be still?)

For the black calf loafer, I’m not sure if this is essential given my tiny collection, but wanted to ask.

Andrew H

Thanks! Do you think the logical small next step is the dark brown suede loafer? I’m not sure if that should be first or the Chukka.

Faz

Hi Simon

This is a great post, thank you. I have a question. I am thinking of having a boot made in the ‘Arran’ style by Gaziano & Girling and wonder if you can shed light on the best material to go for ie suede or leather – I want it to be versatile and something I can wear most of the Year. Further, I’m not clear on whether boots are best made up in leather or suede.

Thanking you in advance for your kind insight.

Faz

Hi Simon

I just have a follow up question. I am using this article as a guide to build out my shoe collection but I have heard the chukka boot is really only a spring / summer shoe. Is this true? As you know I’m looking for maximum versatility and a shoe which can comfortably be worn most of the year and esp in the winter.

Thanking you in advance for your kind time and insight.

Edouard

Hi Simon, would you wear black loafers with denim? If not, why not?

Edouard

Looking forward to it. Thank you.

Amit

Hello Simon. Will replacing option 3. The brown-suede loafer with these https://angloitalian.com/products/desert-boots-chocolate would be an versatile option as well. Also these https://www.thearmoury.com/collections/shoes/spenser-plain-toe-butcher?variant=40504410275911 as an option for – Dark-brown suede derby to wear with Indigo Jeans and Trousers you mentioned above.

Anonymous

Hi Simon

I have a quick question. I have a new pair of Edward Green Galway’s in brown Utah leather. The first time I wore them, someone splashed their coffee all over the shoes in a coffee shop. Accidental but nevertheless painful!

Are coffee stains permanent and, what would you suggest is the best course to mitigate any damage.

Faiz

Hi Simon

I have a quick question. I have a new pair of Edward Green Galway’s in brown Utah leather. The first time I wore them, someone splashed their coffee all over the shoes in a coffee shop. Accidental but nevertheless painful!

Is the damage caused by coffee stains permanent and, what would you suggest is the best course to mitigate any damage.

Lindsay McKee

Take the black and the brown Oxfords. I have a dark brown pair of G&G MTO Regent oxfords in hatchgrain leather. I’m intending to get another pair of the plain Oxford offerings, better fitting, the former being rather tight, but in an even darker brown plain calf but not black.
See my Tim Hardy belt in a recent post for an idea of the colour ….almost black but not quite.
I don’t know whether to opt for patination or not…probably substitute dark polish instead.

What is your thoughts on that please?

Lindsay McKee

Super
Thanks
Lindsay

Iqbal Haikal

How versatile do you think of this pair of saddle loafers is in dark brown suede? Should one just go for penny or tassel loafers instead? Thanks in advance.

IMG_3034
Ken

Dear Simon and readers

Does anyone know what Oxford Calf is from John Lobb Paris? If so, I would appreciate some explanation of the difference between it and their normal calf.

Best,
Ken

Ken

Please check the links below.

https://www.johnlobb.com/en_eu/mens-shoes/liverpool-prestige-leather-sole

https://www.johnlobb.com/en_gb/shop/kensington

The Oxford calf seems to be shinier than the normal calf, and a couple of models in their prestige line were made with it. Given the amount they are asking for, I wish it is not corrected leather.

Ken

That’s odd. I’ve re-attached the links below.

https://www.johnlobb.com/en_eu/mens-shoes/liverpool-prestige-leather-sole

https://www.johnlobb.com/en_gb/shop/kensington

In fact, the leather is a plain black calf with a more polished look.

Thanks
Ken

Samuel

Hi Simon,

Curious if this is instead the 5 loafers capsule wardrobe, what would the 5 be?

Daniel

Hey Simon,

Looking to replace my old brown suede loafers with something new and better quality (they have also fallen apart).

I am thinking of going either with the EG Piccadilly or C&J Boston. Based on my lifestyle (mainly straight denim / straight rubato chinos) – I feel the C&J would be more versatile… but I do have the C&D Harvard in Dark Brown Cordovan which makes the Piccadilly more attractive.

If you could only pick one brown suede penny loafer, which would you pick?

Tom Denny

Love this Simon, thanks for putting it together for those of us really just starting out.

In regard to Chukkas, where would you suggest looking? Edward Green is far too much for my wallet, something in the £450 and under range ideally.

Thanks in advance.

Tom Denny

Cheers! Which C&J dark brown suede model do you prefer?

Tom Denny

Sorry, I was still referring to the chukka boots. I see four models the Chukka, Chiltern, Tetbury and Upton.