Collars are more flattering with tailoring – but do you care?

Wednesday, April 17th 2024
||- Begin Content -||

I’ve regularly worn T-shirts or crewnecks under tailoring over the years. Not as frequently as a collared shirt, but when you’re always looking for more ways to wear suits and jackets, the more relaxed look of a T-shirt has perennial appeal. 

I’ve written before about what kinds of T-shirts and sweaters work. Tips in that article include knitted tees over normal ones, the virtues of pattern, and why double-breasted jackets can be easier than single. 

But one thing I haven’t spoken about much is the extent to which a T-shirt under a jacket is flattering or unflattering. Given this is often the argument put against the look, I thought it was worth a discussion.

Collars are, in general, more flattering on men. The collar frames the face, hides a long or thin neck, and creates that complimentary V down the front of the body. Even if you have a shorter, wider upper body, a smaller collar and the open front will often be the most flattering.

But some people need it more than others. If you’re thinner or less muscular, there’s greater benefit in the structured lines of by a shirt or a jacket (and indeed well-cut clothes in general). I’m personally on the taller, slimmer side of the spectrum, with sloping shoulders, and know that in general a collared shirt is more flattering on me. 

I like the image above, for example, pictured front-on in a knitted T-shirt and suit. But the one below, showing the same outfit from the side, reveals something of what you lose without that shirt collar, with my longer exposed neck. 

Other aspects of your body can also make a difference - not just shoulders, neck and general upper-body. 

For example, as I’ve grown my beard out over the years, I’ve noticed that more facial hair helps this kind of look. Compare the two images below of me in navy jackets and navy tees, for instance. They’re not the same angle, but I think you can see that the second flatters more than the first. The beard helps fill in some of the gap. 

This applies to hair in general. It’s one reason women can get away with a greater range of looks, and I’ve always thought it was why guys with longer hair find it easier to wear hats. 

The gap can also be filled by things like scarves, or collars on the knits. 

The flattering height of a half-zip is one reason they’re so popular, for example, and we all know how flattering a shawl-collared cardigan can be. In the first outfit below the collar of my cardigan effectively replaces the collar, and in the second image a scarf does the same job. 

The other option is to turn up the collar of a jacket, as I’m doing in the PS Shetland Tweed shoot at the bottom. Ralph Lauren does this on all its mannequins, just lifting the back of the collar to frame the neck. But a popped collar is not for everyone, or always appropriate. 

Now as with many things in menswear, the key is to recognise these points - then decide whether you care.

On PS we’ve always argued that fit is an under-appreciated aspect of clothing. But that doesn’t mean it’s the only one: quality, relevance and personal style will always be important too.

When it comes to T-shirts under suits, I put more weight on physical flattery than others and so most of the time wear a collared shirt. But I still switch it up sometimes, just because I feel like it that day. Flattery and style swap places, briefly, in the pecking order. 

For thoughts on what knits and tees look better under tailoring, see previous article here

For more on the necklines of crewneck sweaters, and what flatters you, have a look at the article here.  

Notify of

Inline Feedbacks
View all comments

Very good post! And the picture of the side was so good to understand the effect for me 🙂


I may prefer the shirt but honestly your setting of doing it seems the perfect balance to me. On the images it suits you very good and the side profile is indeed also not purerly unflattering. Doing it with care can look good, one better than the other 🙂
So in the end I would say, even I care most times too much, in this case i am quit relaxed 😉


A very nice read


Aside from the aesthetics of wearing a collar the other big reason is to stop the jacket collar touch the bare skin at the back of your neck and thus causing it to get dirty .
It’s one of the main reasons why , even in the summer months, I’ll wear a collar with a jacket .

In my younger days I wore t-shirts with jackets , probably the ‘Miami Vice’ influence , but looking at those pictures above I’ve realised how much I’ve grown away from it .


I get a bit overly conscious whenever I don’t use a shirt with a jacket, worried that it will soil the colar . What I always do is use a scarf (cotton or silk) to serve as an additional layer . Have the effect of both protection and a bit of face framing , though that can be considered another aesthetic and not everyone will like the association of such neck scarfs


This was a great read – the type of thinking I really appreciate from this blog. It took me a long time to realize why I never looked good in a crewneck sweater – my neck is too long. For knits, I often use a mock neck t-shirt underneath to ameliorate this.

This type if thinking (what flatters me, not what is a good or on-trend garnent) is something that I think women are much more trained in than men. Many of us easily get lost in nerdy things like fabric and construction. This is also part of why ’flat lays’ are so easy and outfits are difficult.

Beyond what you have written on this topic before, I think another reason why tshirts so easily become popular under jackets from time to time is that they are much easier to fit under a jacket. Sleeve length, collar and the body easily make a shirt clash with a jacket. And it is easier to wear a black t-shirt than a black shirt under most dark jackets, allowing you to incorporate that color into your outfit.


A T-shirt worn this way devaluates a jacket in my opinion. It looks like a forced way to make something formal look less formal, no? I admit that may be my eyes though, and as you write it may work better on some physiques than on others 🙂

Peter Hall

I agree with the majority of the opinions-there are never absolutes, but ,think that it is more on the fashion side than style.

Personally,I would go for a knitted polo under a jacket. I think the tee is one side of the arc and a jacket the other.


I actually think the t-shirt with suit looks WAY more forced than trainers with suits. The suit and trainers can make some kind of practical sense. Maybe you realised you had to do a lot of walking, and wanted some shoes that were easy on your feet. Or you were in a hurry when you left the house and just got the shoes that were already out.

On the other hand, the t-shirt with a suit doesn’t give any practical benefits. You’re wearing a suit, so you’re not going to be much cooler by wearing a t-shirt than a collared shirt. And the t-shirt is actually much worse at protecting your suit from sweat and grease from your body. Also, you tend to put on the t-shirt and the suit trousers at the same time, so there’s no real feeling of “oh, I just threw on what was around”. It’s clearly a deliberate choice to wear a t-shirt with the suit. And I can only see 3 possible reasons to do that:

  1. You really don’t know/care. And considering how rare suits are today, I think anyone wearing one is making an active choice.
  2. You were told it would make you look more youthful and casual by a 20-something stylist that reads Vogue and still think that short, slim-lapeled jackets are the height of fashion. This combination has been a standard in high fashion lookbooks for years, after all.
  3. You’re a #menswear guy who is trying to achieve #casualelegance by wearing your #suit with a #knittedtee because you got tired of posting pictures of your #baseballcap and #sportcoat combination.

It simply feels like a very studied look, an attempt to do high-low dressing but making it WAY too obvious. It has that in common with the suit-trainers look, at least.

I think the collarless look can work with tailoring: the reader portrait of James, who wore casual jackets with fine knitwear, was a good example. But he was wearing pieces that were close in level of formality, but in styles that aren’t usually combined (v-neck cashmere and jacket). Wearing a knitted tee with a casual jacket and linnen trousers would be a step in that direction, but the suit+high quality t-shirt will always seem like an overt attempt to dress down your suit by copying a look that has been done to death by fashion brands already.

So in my opinion, not a huge fan. Still making up my mind about the high quality crewneck+jacket look.


Hahahahaha you made me laugh with the last of the reasons… Especially as I never liked that baseball cap with jacket look.
I have done the t shirt with a suit look in the past, but I dropped it as I got more comfortable wearing the suits with shirt and tie (and I also bought a lot more of these two). On the other side, I have never done the sneaker with suit look as I don’t own any.


Glad to hear the humor came through. In all fairness, I have been very #menswear and definitely tagged my social media posts in silly ways! (now I leave the influencing to those actually skilled at it).

I do find that many of the ways to dress down tailoring look very forced to me: baseball caps with jackets, tshirts with suits, sneakers and suits, and the only-seen-in-lookbooks-and-social-media safari jacket with a tie!

I think the secret to dressing down tailoring is that the combinations have to look organic, like something that could occur naturally, as well as giving some kind of benefit. Wearing a jungle jacket over a suit can look like you threw on some extra outwear because of the weather. A tweed jacket with jeans is practical (so many pockets). Tees with suits, dress shirts with jeans and ties with anything look intentional.

20- Something Year Old that reads Vogue

The tee with suit combination has been standard for a very long time in fashion because it works as a legit attempt to relax the formal connotations of a suit. I can tell you now that wearing a tee with a suit is not a sure fire way to make you look “youthful”, I’ve seen it go wrong many a time it has to be considered and thought through. Trainers and a suit is a far more forced attempt to look youthful and relaxed that just comes off sloppy. Personally a sport coat and tee is a go to because it keeps things simple.
Also short, slim lapel jackets died out a while ago.


Love your username!

I think we’ll just have to agree to disagree about the tee and suit – to me, it always feels like the equivalent of an academia-speaking college professor adding a “fo shizzle” to his jargong-laden presentation – a too obvious, too incongruent addition.

I think the sport coat and tee that you describe can work better, especially if the rest of the outfit bridges the two extremes. Last month I was invented to a upscale department stores “trend talk” (as a guest, not a speaker!) with some fashion journalists presenting the seasons “must haves”. The talks, the must haves and the personal style of the fashion journalists were all terrible (and there were still slim lapels on some jackets, clearly THEY don’t read Vogue!), but towards the end they had a young man who actually worked at the store talking about shoes for spring, and he rocked the tailoring and tee look: it was very tonal (putty trousers, white tee, oatmeal jacket, mid brown shoes and belt) in fairly casual materials. Everything looked natural, like he just wore things that fit and worked well together.

Compared to the fashion journalists (one who wore the most ill-fitting suit I have seen in the wild, and the other who spoke about how cool he was because he wore his club blazer with a hoodie and stretchy, pre-distressed jeans (and dirty white sneakers)), the guy was an epitome of quiet style. It worked because it didn’t seem like he was trying too hard.

I don’t think it would have worked as well with a suit. Like I said, in my mind these things only work if they look like they occur naturally. Dressing down tailoring is like being cool; if it becomes too obvious you’re trying, it has the opposite effect.


Really enjoyed the exchange (above). Brilliant contributions.


Good article.
I think it’s almost more important whether a crewneck collar is tight / high or not. Low collars can look sloppy and are probably not very flattering for most men.
I’ve had good experiences with the merino T-shirts from Colhays or the T-shirts from Anthology, but also with the casual PS T-shirts, which all have a tight collar. In my opinion, a merino turtleneck is even better, but that’s not really an alternative for the summer.


I prefer the look of a jacket with a collar (my neck is also on the longer side). However, I take the point that wearing some kind of crewneck increases the versatility of tailoring. It works best with outerwear, not just overcoats, but even when jackets are used as outerwear.


For me a big part of this question has to do with communication and approachability. I’m one of the last to still regularly wear a tie in the office. But this last year i have really noticed that some people have strong feelings about suited men, and not in a positive way. Sure, a suit with collar looks better, especially with a tie. But it signals something you might not want to be signalling. This made me rethink my office attire unfortunately, as i don’t want my clothes to hamper my performance. If i want to look approachable i will avoid ties, maybe even collars.

Paul K

I’ve had the same experience in recent years, after having moved to a warmer climate. When I wear a tie, I draw attention in ways I don’t care for, whereas in the past there was a general unspoken appreciation for my professional wardrobe. Accordingly, my entire wardrobe is shifting and I have lots of mixed feelings about it.
That all said, I will never wear a tshirt of any kind underneath a jacket. It just doesn’t work for me. A really nice polo, though, I am doing a bit more of—but only with my more casual jackets.

Zach S

Nice article as usual, some interesting thoughts.
Personally not comfortable wearing a blazer without a collar so far although I do of course frequently wear a t-shirt with more casual jackets (i.e. bomber or military-style). Then again, I usually pop the collar on those and have started to enjoy wearing more scarves in that case. Either way, a wool knit polo (or indeed occasionally an ordinary one) is about as far as I’m willing to go on that. Frankly, it’s often even my favourite way, maybe largely because I don’t have many smarter occasions to wear a blazer.
Also, in one of the last paragraphs you wrote ‘that fit us is’ – I’m assuming the us was unintentional? Unless I’m reading it wrong.


I care! It’s only recently after being influenced by PS that I’ve started to wear crew neck jumpers with only a white t-shirt underneath (I’m still seeking the perfect slither of white peeking out!). I’ve always previously worn a shirt as I have what I think is a long (and 15.5 inch collar) neck and believed that a collar helped to shorten my neck and looks more flattering.
Also, it’s a practical matter where a coat or jacket collar is kept cleaner by not being worn directly against the neck. I’ll wash a shirt after every wear. I’m exploring more casual clothing/workwear and not wearing a shirt underneath a jumper is part of that and I like the experimentation. I’d like to try a neckerchief but not quite there yet and do not want it to look like I’m wearing a cravat. On others a neckerchief looks great and presumably solves the issue of a jacket/coat collar getting stained (suncream/face moisturiser etc).
I see heavier-set guys with no or a very short neck wearing a shirt with a collar and the collar ends up round their ears esp. when they’re sitting so a crew neck option would look better on them I reckon.
Indeed that pic of yours at event with a jacket and crew neck top shows the difference and imho doesn’t suit you as well as a collar. I hope you don’t mind me saying. As we have a similar build it helps me to appraise how I might look.
I like that you write about these matters, to those of us who follow you it *is* an interesting topic!


I do find that collars are considerably more flattering for me. However, I believe the larger issue is the dress/attitude correlation. I have found that when I wear a t-shirt (even nice merino examples) I feel underdressed; when I put on a collared shirt I feel more determined. I have even taken to having my shirts made with a very specific collar that is at its most flattering when it’s worn casually. So whether it stems from some sort of self-consciousness, or even snobbery, I believe the way I carry myself based on a collared shirt is the greater factor when deciding which shirt I choose.


Hi Simon,
thanks for another interesting and useful article.
I don’t recognise the jacket yourself wearing with the white jeans. Where is it from and have you written about it?


Another slim necked guy here, and I feel your pain. I often try tees under jackets and have found that success often comes down to the type of collar on the t-shirt. The heavier bound collar and higher back on the Permanent Style t-shirt, for example, look great with a casual unstructured jacket (possibly because the tees are almost crewneck sweater weight). Lighter weight tees with thinner collars just seem to make a thin neck look even thinner.

Mark Seitelman

I don’t like the look at all. It looks unfinished. I find the look odd, i.e., wearing a suit coat or odd coat with a t-shirt which has it origins as underwear.
Wouldn’t the collar get stained with skin oil and perspiration?


Surely a lot has to do with your age? In general, I think certain “looks” are made better/worse by the person wearing them, and that has a lot to do with their age and condition.What looks good on a well preserved 35 year old will not necessarily look good on a slightly portly 50 year old.


Yeah, “a long time ago” for you, young man… not for all of us 😉
Though, I believe I’m not much older than you, still, I agree with Mark.
And, you’d have to admit, that in an overly casual era, your wardrobe is dominated by what many would call clothes that appear “from a long time ago”.
(I bemoan this just as I’m sure you do.)
Thus, if we (you, me, your readers) are going to keep sartorial tradition afloat, we should harken to it’s time honored rules.
I’m with Mark that even in 2024, as commonly worn as they are as outerwear, a T-shirt is still underwear… unless it’s hot as heck outside, then fine…
I say this all in a friendly way, you understand. I appreciate the opportunity to throw little jabs at your outfits!

C C Chandler

This qualifies as a “no brainer”!

Joshua Grindatto

This is enlightening for sure!

In my industry (software) collared shirts can often put you over the edge of “too dressed up” if you’re wearing anything other item that’s a bit more elegant (leather shoes, real trousers, a sport coat(!)) so a t-shirt is a great alternative.

Thinking back to when my Dad was working in software in the early 00’s as an executive he always was wearing a soft suit or jacket and trousers with a fine knit underneath and I think it balanced his position with the casual work so well! That being said he’s a full bodied 6’6” Swiss mountain man so his neck fills in the jacket nicely like you pointed out.

Eric Michel

Few years ago you would have been under arrest by the Style Police for wearing a T-shirt with tailoring, those days it is wearing a tie which makes you a rebel. I have been wearing T-shirts with tailoring or ties depending on occasions since I bought my first jacket. I like Miami Vice as much as Mad Men, and Giorgio Armani has been wearing T-shirts with tailoring forever, and has always looked great, then nothing really new on my side…


Definitely a relatable article. I’m also slim with a long neck, but I am not overly concerned about dressing myself in the most flattering way possible these days. I find it too limiting to think in those terms, I would rather have fun and enjoy what I wear.

Markus S

@Simon. Just for your information. There are recently two readers named Markus – a common name in German – who comment and not one who comments so much it’s annoying. I (Vienna lawyer) will therefore post as Markus S. in the future.


For what it’s worth, I think the fuller beard ages you. A lot. The trimmer look is far more flattering on you.


I think quite the contrary – the fuller beard is a massive improvement, mainly for the reasons you say in the piece. Generally, I find you look a lot better than you did in images from 10 years ago.
On the question of wearing a shirt without a tie rather than knitwear under a jacket, I find there are added levels of complexity. A shirt collar does frame the face better, but then does it fit into the jacket or pop out, as it does in a few photos in your Vittorio Salino tweed jacket review, the second last image in the piece illustrating the problem most obviously? Can you wear the shirt with a crewneck beneath it, or then do you have that weird thing where one button too many undone under makes it go wonky, but if you do that one up you look like a priest. Or a v-neck, and then you might look like a schoolboy. Or with either, the jumper being too tight and the shirt looking all lumpy beneath it. Or the jumper too loose and now you look like you’re in a Nineties indie band. Or no knitwear, but then when you sit down the buttons protrude at the waistband, and when you stand up again they are all out of whack and you look paunchy and a mess. Or you are cold.
For those reasons and a few more, I tend to wear knitted polos, crewnecks, or rollnecks, all of which I find have far fewer issues and just give a simple and elegant look without as many pitfalls. As you’ve written about yourself, a rollneck is particularly flattering with a jacket and gets rid of the neckline issue.


Two of the three Bee Gees sported short, trim beards in their heyday of the ’70s.
In an interview, one of the them joked that their short beards were “nearly beards… as in: the nearly beard gets the worm.”

Lindsay McKee

It’s a collar with a jacket for me.


This is a really thought-provoking read, Simon. Thank you. I had certainly never considered myself as fortunate simply for being able to wear both collared and uncollared looks, although I certainly now feel that way having read the comments here.
Both looks are equally stylish when done well, but in different ways. Context feels important though – where are you going, what are you doing, who are you seeing?
I do believe that people take someone wearing a collared shirt more seriously and generally treat them more respectfully, whether consciously or otherwise.
Working in a very casual environment I am more often than not overdressed, but I wouldn’t look favourably on someone attending a job interview without a collar, even if I know they’ll almost never need to wear one should I hire them. Social conditioning is clearly very powerful!


That is a very interesting point, Simon. I don’t know how many readers you have in their 20s at the start of their careers – I’m guessing not many? But it would be very interesting to have an article about how to calibrate your workplace look based on your relative age/level/ambition. In fact, it would be interesting to have a workplace series full stop! I know you have done a few pieces like this one:


Simon, the first photo looks the best and it really works for you.
I’d just say that from an American’s vantage point, the look was overplayed by Don Johnson’s character in Miami Vice in the ’80s and still has dated, flashy nightclub connotations for me. It’s Tradition giving up too much in a bargain with Modern Casual, if that makes sense.
Still… the top outfit looks sharp.


Just giving a data point: I’m 33 and I don’t get that association. However, one that I do is the combo navy jacket+ T-shirt+ skinny jeans that often appears in smaller companies (at least in Brazil) and in tech, and I must say that I don’t like it . Most of the time it is the fit problems: slightly overweighted people with skinny jeans, and tight suit jackets serving as sport jackets. But as this happens quite often, even if the fit were good, I would still associate to those that aren’t and wouldn’t like the combo.

Guy W

A nice extension of some of your other articles, Simon, and very useful for exploring t-shirts/knitwear under tailoring. I’ve been exploring this more and more using your articles as a guide, which have been useful in being able to do this in a more ‘put together’ way (i.e. not looking like the average guy who throws a regular t-shirt under a tailored jacket).
On the question of neckline, you mentioned that yo might do an article on how to wear a bandana/square scarf. I’d definitely be interested in this.


Nice article! I found the photo of the article on the main site intriguing: three men with similar colors and clothing, but three distinct styles. Luca at the left with a collared shirt, you in the middle with t-shirt, and the men to the right (I don’t recognize him) with a mock neck (and what looks like a unstructured blazer?). Each is a well-executed, but quite distinct, style to me.


Beginning to care more about what flatters my body, I actively enjoy wearing collars nowadays. Of course there are some looks that just look great with a t shirt (i.e. with jeans)!

I work in a relatively lax dress code industry but where collars are still the norm, even if it’s in mass produced company logo Polos or low rise collar button ups. Hardly anyone is wearing what flatters them most! In contrast, women in the office know how to dress much better in this regard. Truly a shame for the men, as they show how it can be done day in and day out.

So, for me, wearing what flatters me gives me confidence and helps me feel unique in what I’m wearing, even if it still falls under the same “style” as everyone else.

Disclaimer, I practically never wear a jacket at work, only interviews nowadays. However in my personal life, I will wear a t shirt with an slightly oversized shirt or shacket to emulate the layers of shirt and jacket, and keep some kind of collar, even if unbuttoned.


Ah, yes, absolutely! I can’t stop at this point… haha

Another point on collars and necks that I wanted to add is that color makes a difference IMHO.

For example, wearing a mandarin collar shirt in light colors (ecru, white, sand, light blue) against my pale complexion reduces the contrast with my neck and makes the division that would otherwise highlight my longer neck less apparent.

Whereas a dark color really highlights a lack of collar saying “neck starts here”!


Do you know the exact trouser cloth in photo 4, where you are standing in front of the fence? What color would you describe it as?


Any chance you may kindly be able to find out? By the way, it looks great!


I’m curious to know what shoes you wore with the first two outfits.


It’s funny reading this article, because I’ve always thought you look really good in a t-shirt with suit jacket! Dare I say, I think I even find it one of your best looks.
Though I see what you mean with the picture from the side, I do not think that is necessarily a bad/unflattering thing.
Interesting to read your own perspective on it though.

James S

What is the navy jacket you are wearing? Very nice!


Perhaps counterintuitively I much prefer the look with the suits when the t shirt is of similar tone. Much less so with the odd sports coat. I also really like the looks with the overcoat and Teba but you could argue the shawl collar and scarf are “collars” of a fashion hence why the looks work.

William Kazak

I have long hair and wearing a hat looks awful on me. I can wear a flat cap if I have to keep warm if I pull my hair back behind my ears. As we get older that “chicken neck” appears. Collars are great for that although it is so often very convenient to just wear a crew neck sweater or a t-shirt.


I appreciate both viewpoints, but honestly, I despise the t-shirt under suit (or odd jacket) look. Not only do I find it less flattering and incongruous with the jacket’s formality, but it’s reminiscent (at least here in the States) of vice cops and club bouncers.


Yes, I do like the T-shirt jacket combination, I do wish there were more T-shirts with a higher neck, not quite a mock turtle neck, but enough fabric around the T-shirt neck so the jacket collar doesn’t sit on your bare neck.


I also blame “Miami Vice” for making anyone even think that it might be a good idea to wear only an undershirt under a jacket. I launder shirts regularly: Dress shirts worn buttoned generally need washing after a day unless you want permanent stains on the collars that will never come out. I clean jackets seldom, as little as possible to preserve their tailoring (dry cleaning also takes a toll). The conclusion is simple. Unless you want to destroy your suits and jackets, wear a collar.ed shirt. As for looking better, degustbus non disputandum and I won’t inflict my opinion, but as we get older, the less seen of the neck the better. I would never go full on Lagerfeld, but finally fully appreciate ascots… T-shirts leave nowhere to hide.


Hello. I hate to question you, but surely chambray is white warp / coloured weft?
Secondly— tee shirts under a jacket:- Due to natural oils in the skin, this must lead to staining on the jacket collar, and therefore excessive cleaning of a tailored garment — not ideal!
regards. GWO


Nice article – and I appreciate your posting “unflattering” shots to illustrate the point, helps to keep things real and relatable.

I think I have a long slim neck and prefer collars generally. I also have fairly broad chest/shoulders and a smallish head so I’m still figuring out what looks best. With now-thinning hair I am stuck between wanting to keep it clean and wanting some volume to avoid looking like the mondoshawan (I had to look that up) from The Fifth Element. On that note, I also don’t quite know what hats are actually best and most practical for me (I enjoy tweed flat caps). Fun stuff.


There are more factors here than just smart/traditional vs relaxed/modern. Many guys look simply awful in a t-shirt if they are overweight and in that regard a traditional shirt will better disguise a Dad-bod.

There is also a natural line in a jacket that leads the eye from stomach to chest to shoulder to neck to face. A mock neck jumper or t-shirt continues that unbroken line, whereas a round neck standard shape of t-shirt breaks it. Although you’re still quite slim and a decent looking bloke, Simon, so can get away with more, I still think you down value some of your expensive and beautiful jackets by wearing round necked t-shirts with them. The jacket often screams ‘I tried so hard but he broke the line at the collar’ in many of the modern wear shots I now see on PS. Your longer neck in my view needs a mock collar or polo neck or a cravat or scarf to avoid the break in the line I refer to. The alternative is, as you allude, to turn up the jacket or coat collar which is in my view is just trying to compensate for what went wrong in the first place.

It’s no coincidence that high quality menswear has always framed the neck – be it a lace ruff of the sixteenth century, the stock tie of the seventeenth – nineteenth centuries, the bow tie or standard modern tie of the twentieth or twenty-first centuries. Men simply look taller and slimmer with that seamless look from waist to face.


I’m wondering whether you have had to pay any particular consideration to the sleeves in these looks, Simon?
I’m thinking both that a long sleeve t-shirt might be nicer to wear and appear under the jacket cuff a bit like an ordinary shirt (I’ve never got on with short sleeves under a jacket, personally).
But also that perhaps a jacket that has a slimmer sleeve itself might be easier to wear with a t-shirt (whether long or short sleeved), because either way there will be less cuff and shirt sleeve with which to fill it.
What do you think?


One thing I’ve really taken from this article is the power of associations. A few posts refer to Miami Vice – excluding the movie, this predates me but it looks like it came out 40 years ago. With this in mind I’m going to push myself to test my own associations/ prejudices to try to keep a contemporary view on things. Overall it think this is good to have as an option in the formality hierarchy so thanks for highlighting how it can be used.


While it’s a bit before your time, and that of many of your readers, I think it’s an interesting topic. While it was hard to make handsome actor Don Johnson look bad in anything, his look came at a pivotal point in menswear… again, at least from an American vantage point.
The aim then I believe, and with many men mimicking the look back then, was to dress up while not appearing overly dressy. In other words, “the Mrs. wants me to dress up a bit for our night out… but I don’t want to look too fancy.” And thus, a compromise was reached, in the sartorial sense. And, ugh, what a compromise it was.
Compromises can be a disaster: dress down in jeans and a t-shirt… or dress well.
In my view, you rescue a look I generally don’t like, because of your signature, highly focused attention to tailoring. Your jackets, their lapel taper and roll, etc., are generally so lovely that you could wear them over nearly anything, heck a ratty old sweatshirt, and the outfit would still work quite well.


Well said Leif. I frequently get comments from friends about how “uncomfortable” (both physically and socially) they are in collared shirts, and it’s a viewpoint that is so utterly alien to me that sometimes I question whether they can really even believe it themselves.


Interesting and thoughtful write-up, thanks. The photos in the article look nice, so I guess it is possible to pull the combination off without looking like a street magician or indie musician stuck in no-man’s-land (career-wise and sartorially). Not wearing red Chuck Taylors also helps, but moreover, so do those excellent brown suede boots.


I think this is why a roll neck or even a mock neck under a jacket tends to look good to me while a non-collared t shirt doesn’t – the high neck does the job of a collar in that look so it results in a face-framing effect that t shirts can’t achieve.
Though in a pinch, a thin silk neck scarf could do the same thing, as others have mentioned – create that higher neck or V line down the front and you have it.




Honestly, Simon, what dictates if I am wearing a collar or not is entirely based on whether I have shaved or not.
I just can not find myself wearing anything that touches the skin, regardless of how professionally it was done.

You raise an interesting point about raising the collar of the jacket, which I will gently experiment with.



Great article. I think a t-shirt under a jacket looks fine in all photos, just not for me. I’m older and my neck is – well – scrawny (what a great word!). In the heat of summer of course I happily wear just a t-shirt, needs must. But under a jacket I never do. I often opt for a mock turtle which draws attention away from the neck, but doesn’t have the “James Bond look” that a full turtleneck does. In fact I prefer this to an open neck shirt which still looks somehow incomplete under a jacket, the line down the placket always looks messy IMO. This can be easily rectified by also wearing a waistcoat or very fine merino v-neck. Magically, the extra v-shape makes everything look put together and the open neck shirt can look great.

Jack Linney

I have never been interested in wearing a tee with a sport coat. The most prominent reasons are practical. First, no matter the sport coat’s fabric, I find bare skin hitting the collar to be uncomfortable at the neck. Second, with a 49 (or so) inch chest and a measly four to six-inch drop (depending on my ever fluctuating weight), a plain tee focuses attention on my breadth.
The final two reasons are the look. First, I find that tees don’t stand up well against sport coats. Even the floppier “heritage” collar, which occasionally do something of a disappearing act when paired with a sport coat, frame the face better than a sport coat. Second, I never liked the cheesiness of Miami Vice, and tees with sport coats remind me of a show I’ve no desire to revisit.
All that said, I think tees and sport coats are a matter of preference. Perhaps the look might favor someone with a different body shape than mine.

JJ Katz

Interesting post. The thing I don’t get about t-Shirts (especially with tailoring) is simply: why?
They are not significantly more comfortable or easier to launder than a collared, button shirt. OK, one doesn’t have to iron them but the convenience vs. elegance trade-off seems completely imbalanced, to me.

I can understand chaps wearing casual chinos (where applicable) over tailored wool or linen trousers for convenience purposes, for instance. But T-Shirts?

Jim Bainbridge

I wear a (casual) collared shirt most of the time, but I feel similarly about exposed neck with a t shirt as the shoulders in an unstructured jacket (which I also wear most of the time). To my eye, more unusual (but not wrong; at least in a bad way) is the same t shirt with a strong shouldered jacket.


Hi Simon, I noticed on IG that you were wearing the black denim Rubato shirt. Since you wear it, I am assuming you like it. What’s your take on a black vs indigo blue version? This one seems nice but I was wondering how bold / unusual the black version is vs a more traditional blue denim one, with the black buttons, etc. And assuming that a black shirt is easier to wear in this fabric, as it is with other ather textured ones, eg corduroy, linen…


This will probably be considered a tangent, but i was wondering what you, Simon (and the other readers too), think about collars worn outside/on top of the jacket collar.


‘Agree, for most situations. The only time I think it can be pulled off is in very casual situations (like when it’s a polo underneath a relatively casual jacket, and the contrast is low).



Hi Simon, hope you’ve been well. I recently purchased the finest polo and it works unbelievably well in the humidity. Regarding the topic of t-shirts, I wanted to ask if you’d know whether something like the Rubato knit tee/anthology tee would be as breathable or suited for high summer as well? I’ve also tried The Armoury’s ice t-shirt but I found it a little too thick for 30+ degree weather. Thanks!


i believe M Armani has often worn the navy tee and navy jacket. Looks very fine on him whatever decade you choose. I think it looks very natural
although I am more traditional i have used that look often and feel surprisingly at ease.
the lack of collar is a nice change.

Bob M

I think “it depends”.

Wearing linen or cotton jackets, it looks fine. Under a dark navy banker’s suit, it looks out of place.

Case in point. At lunch, a decent fellow shows up wa navy blazer and pocket square, torn jeans, and dirty sneakers. Can you say “conflicted”?

If you’re going to convey an image, be consistent. Cut, fabric and texture should work together… not at odds.


Never been able to handle the t shirt or sweater with a coat / jacket thing.
Showing my age but I always feel it is Miami Vice.
1) Almost always wear a collared shirt, of wildly differing levels of formality.
2) When I wear only a t shirt or sweater I wear a blouson, leather jacket, wind breaker etc. Or nothing with it.
3) Hate feeling of bare skin on suit coat, sports coat or blazer. And as someone said below it’s sort of dirty too.

John Smith

I think that unless you’re as handsome as the author of this article, you should always avoid a t-shirt and a tailored jacket. Cheers.