Ian is retired, and got into luxury menswear late in life. But he always had an interest in clothes, from his early days in Ivy clothing to the forties and fifties influences that came with learning jive dancing. 

It could be easy to see him as being able to wear whatever he likes, just because he's retired - but it became clear when we chatted that Ian has always dressed his own way, even if it was something simple like wearing his horsehide Eastman when he was driving the Tube.

Warm and chatty, Ian is a real pleasure to talk to, and I encourage anyone to do so that sees him around London. I hope you enjoy our conversation as much as I did. 

Outfit 1: Bespoke and Fred Astaire 

• Hat: Bate’s
• Glasses: Shuron
• Suit: Anderson & Sheppard
• Shirt: O’Connell’s
• Tie: Vintage, hand-painted silk
• Shoes: Tricker’s for Mark Powell

So Ian, I hear a real estate deal launched you into luxury menswear? 

Ha! Yes you could say that. I owned a house in Ealing that I'd bought back in 1978, and sold it a few years ago when I moved in with my wife in Islington. That made quite a lot of money. 

When I did the sensible thing and talked to a friend who worked in investment, he told me just to spend it, so that's what I've been doing! I didn’t need telling twice. 

And what was your first extravagance?

It was a bespoke suit at Anderson & Sheppard, the heavy navy flannel I’m wearing. For a man the ultimate has to be a suit, and that means Savile Row. I chose Anderson & Sheppard largely because Fred Astaire has always been my idol.

I told myself I’d just get one, for the experience. But it’s ruined me - I used to wear a lot of vintage tailoring but I can’t do that anymore, you just notice all the places where it doesn’t fit, often on the back of the neck.

So I’ve been back six times now: five suits and one tuxedo. The latter was a copy of a vintage one I had, and they did a good job of replicating all the details. Even on this suit, I asked them to replicate the style of an old pair of Hollywood-top trousers I had, with the drop loops. 

Oliver was the trouser cutter - I think he’s at Marinella now - and he loved them, he’d never seen anything like it. 

Where’s the tie from?

That’s vintage, a birthday present from Terry Murphy - the late Terry Murphy - who ran a vintage stall in Camden Market, real high-end Americana. It’s hand-painted silk and probably worth - actually I have no idea what it’s worth, it probably depends how many people want it. You see these for over £100 on auction sites, but then in markets for £2. 

The shoes are from Tricker’s - Fred Astaire used to wear blue and white ones like this, though they were slightly different: the collar around the back was blue too. 

You won’t be surprised to hear I watch a lot of old movies - I was rewatching The Red Shoes recently and there’s a great section where they go to the Riviera, very relevant for your recent articles. 

The film is OK - Moira Shearer can’t really act, she’s just a great dancer. But those films have such depth to them, there’s always something you pick up on, especially in the clothes. 

What did you do for a career, before you retired?

I’ve never followed a career really, I’ve done all sorts of things. I got a degree but I never used it. 

My first love was music so I worked in record shops for a few years, until around 1980. That was when they all started closing down - one of the first big waves of record-shop closures. I was unemployed for a while, worked on a market stall, then became a postman for five years.

I wasn’t very good at it: I could never get up in the morning. I’m always on time - friends know that and if I’m a minute late, they go. But the mornings were the problem for me; I became famous for always being late. 

Then I got headhunted by a friend who worked in music, delivering records in a van - on the other side of the counter as it were. I was white van man - well, red, a big Mercedes van. I’d call round independent record shops and deliver records. Reggae mostly, a little house, some garage. Whatever we could get hold of. 

It was pretty full on, 24 hours a day. Some of those places only shut at midnight and they’d call me up, knowing I’d always deliver. It was fun though, good times. 

And you later became an Underground driver?

Yes that was after that - I became a driver on the Underground at the age of 50. At that time 50 seemed old, and I only thought I’d do it for a few years, but now I’m over 70 and 50 seems really young! I retired after doing that for 17 years.

Outfit 2: Summer jive

• Hat: Thomas Farthing, linen
• Shirt: Sun Surf
• Vest: Henri
• Trousers: Thomas Farthing, linen
• Belt: Anderson & Sheppard, braided leather
• Shoes: Doek
• Bandana: Vintage, from Hunky Dory

This second outfit looks like something for much more active dancing. Was it your love of music that got you into that? 

Yes pretty much. I was taught to dance originally by a couple of guys from Grenada that I used to hang around with, in the late sixties. It wasn’t ever reggae back then - the term hadn’t even appeared on the horizon - just rock steady. 

They taught me the basics and I went on from there, always dancing. The other big turning point was when I learnt to do a rock ‘n’ roll jive - which is obviously a partner dance, and comes with a whole world of style. 

Before that I had always been a bit Ivy League, maybe with some Italian influenced - I used to always read Italian Men’s Vogue. 

Sort of like the Continental Look that brought that influence to America?

Yes, just a little bit later, seventies not the sixties.

But that all went out the window?

Yeah I don’t tend to do things by halves! All the Ivy League stuff went, all the J Press suits, and I bought a lot of vintage suits and shirts instead - and I’ve been on that path pretty much ever since. 

Are you ever afraid it can look like costume?

I know there’s that risk - you talk about it on Permanent Style - but I think a lot of the people that look like they’re wearing costume just haven’t got it right. I see them at events and they’ve bought clip-on braces, a hat from a market stall for five quid, a pair of black-and-white shoes for £20 from TK Maxx, and it looks pretend. 

So is it about quality, or style as well?

Both I think. You see the style problem with brands - they want to recreate all these sixties and seventies youth movements, but they never get it right. They don’t bother to do the research and it looks like an imitation. 

I guess there’s always going to be that period risk, but it helps a lot if everything works and you feel comfortable in it too.

Exactly. Find the original stuff, hunt down a nice Arrow shirt or something rather than a modern polyester. 

Is your shirt Sun Surf?

Yes, one of their limited editions. Comes in a nice box, a complete reproduction - well you know what the Japanese are like, so it has the same label, the same hang tags. You don’t really want to get rid of the box really, you want to display it somewhere. 

I think the design is called Land of Robots, but I’m not 100%. The only robot I recognised was Robby the Robot, but I have a friend who’s into science fiction and he could name all of them. The only one I recognised was Robby, from Forbidden Planet. 

Where’s the vest from?

That’s from a street market in Grado, in northern Italy. My wife’s family are from there so we used to go quite a bit. The brand is called Henri - Henry but spelt like the French - and they do good quality underwear, all made in Italy. 

I only buy the vests but they do T-shirts and all sorts. And they ship to the UK, and they’re quick, and cheap! I know you can spend a lot of money on a singlet, or you can go to Primark and get one for £1, but these are cheap and they last for years. They go a bit yellow eventually, but only after a long time.  

Outfit 3: Blues and leather

• Hat: Vintage, JJ Hat Center
• Sunglasses: Shuron as above, with Shuron clip-on
• Jacket: Eastman, Star Sportsman A-2, horsehide 
• Shirt: ‘Skipper’ by Wilfson Brothers, vintage gabardine
• Belt: Vintage, Grado market
• Trousers: Vintage
• Shoes: Sanders
• Watch: Omega sixties Constellation

This looks very comfortable, but then you look very comfortable in all your clothes - something is kind of hard to portray in pictures. 

Thank you, and yes it’s a good thing to raise. As you often say on Permanent Style, it makes such a difference to looking good. 

You see guys at weddings now, squeezed into these suits and ties, and it’s obvious they don’t normally wear a suit. They look like tailor’s dummies. Whereas even when I was working on the Underground, and had to wear a uniform, I’d relax into it, make sure I felt comfortable. 

I used to be very careful with things, but now even if it’s a £4,000 Anderson & Sheppard suit I try to forget about it. 

Did you find it was hard to feel relaxed straight away, for example when you first started wearing those forties and fifties clothes? It can take a few times of wearing something to feel comfortable - but then you’re also not sure how long is too long. 

Yes I guess I did, but age is a very positive thing there. I couldn’t care less at my age. Younger people get physically assaulted for wearing things that are different, especially outside of London. I know lots of people who got beat up for being goths or whatever - they end up moving to London just to have a sense of anonymity. 

I don’t want to sound big-headed but I get people come up to me and compliment me on what I’m wearing. I get abuse sometimes too, but it’s much more the positive side, which I think is lovely. 

I guess you’re always going to draw some kind of reaction dressing that unusually. 

You are, yes, and I’m probably lucky I don’t get too much of the negative. Maybe I just give off some kind of threatening presence when I walk! My wife always says I look miserable and aggressive but I’m not.

This Eastman jacket looks especially comfortable. How long have you had it?

About 10 years, and it’s had a lot of wear. 

Yes it’s at that nice point where it almost looks like vintage. 

True. I have three but this is my favourite. I actually have a G-2 as well, but I didn’t wear that for about five years after Jeremy Clarkson started wearing one - he ruined it. I was told his stylist went into American Classics and bought a whole load of stuff - there’s no way he would have picked that out on his own. 

The hat looks vintage too, is it?

Well spotted, it’s from JJ Hat Center in New York. I went in once and they had this little vintage concession in the corner, a kid was running it and he’d clearly been given his little space to get on with whatever he wanted. 

This was $50 but the hat band was ruined, the leather on the inside was coming away. Thing is, they’ve got this great archive of materials in the back, because they’ve been around so long, so he went and found a new band - and matched it exactly. They reblocked it too, relined it, replaced the sweatband. Great job. 

Thank you Ian, it was great chatting to you, and see you around Chiltern some time. 

I’ll be there, see you around Simon. It was a pleasure.