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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. 


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One of the best ever.

In the first picture with the leather jacket the handrail behind him made me think he was holding a sword or something. Very Indiana Jones!

Tim Jackson

Thank you for this. This really cheered me up. Positive and life-affirming. A fantastic reader profile. Age should be no barrier to being comfortable in your own style.

Matthew V

I agree. The older you get the more relaxed you become, Well I have!


This man has cracked it, his very own style, 100%, no doubt about it. The playfulness, the freedom – but also the unavoidable realisation that in the end, there are no shortcuts when it comes to tailoring. I’m almost 50 but still searching, pondering, no way near as steady.
Thank you Ian, for showing me the way ahead!


Hi, Good to see a more senior person featured – I’m 67 btw. Whilst not necessarily my style or approach as in creating a very strong overarching theme, it’s interesting in as much as how one should not be afraid to experiment and push boundaries at any age. I’m sorry to hear Ian has had some insults that’s unforgivable. Thanks again for another interesting profile.


A great profile and nice to see someone whose style is inspired by the 40s and 50s featured. My own style journey started when I was inspired by the sharp suits and hats in black and white films from that era. I don’t wear much vintage anymore but it always holds a special place for me. I never expected to see that style covered in PS, so Ian’s profile was a pleasant surprise.

Ian’s comments about people getting abuse for how they dress certainly resonates. I got my fair share of that when I wore outfits similar to his when I was in my late teens. Age and greater confidence have definitely helped with that.

JJ Katz

Love this. Very much the way I think many people who like retro clothes think and implement their passion. Stylish guy and great looks.


This line made me smile “My wife always says I look miserable and aggressive but I’m not.”
My favourite outfit and in my opinion the most wearable is the last one. The hat works best here and the leather jacket gives it character. Ian looks great and hats are obviously his style, but for others this might look more natural than for example with a suit.


Wow !
Ian is a veritable style sensei. Of that there is no doubt.
He has an incredibly well honed sense of what works for him and has refined his look over many years. He is completely comfortable with himself.
Would I wear everything on display ? Absolutely not. I’d only wear the suit and the Leather jacket but that’s not the point, I’m not Ian. Ian is and on him it all looks magnificent.
Bravo Simon on finding Ian. Let’s have more ‘mature’ examples. Frankly they are much more interesting.


Wow! Simon, thanks for writing this, and Ian, thank you for showing us your wardrobe. To me, this is what dressing well is all about. That A&S suit is amazing (love a Hollywood top trouser) but most of all Ian looks fabulous and very, very comfortable in every outfit. If you can attain that, then mission accomplished.

Rowan Morrison

I don’t think he dresses “that unusually”, I’ve been to raves and fetish parties so I know about dressing unusually. With the possible exception of the third outfit, which as it happens might be quite suited to a certain subset of fetish parties.


This one was a real treat, thanks Simon.

I always enjoy hearing the background and details about the reader in question, always so interesting, Ian seems to have lived well, lived full.

I also find something to take style wise from all the reader profiles. Ian has a unique style, big nod to the past clearly but it all looks fresh.

The Eastman A-2…. something else, there won’t be another Star Sportsman on earth that looks like that, only getting better too. The beauty of a high quality leather jacket, just keeps giving.


Hi Simon,
Thanks for this profile. I’m always amazed by the sheer diversity of PS’s readership! At some point I think it would be a good idea to work out a survey (with Bruce Boyer and Michael Drake) that would give us at least a rough picture of this communtiy of learners that make up this readership.
It would be of great interest to a great deal of stakeholders, and not merely the readers.
John .


It’s been a long time since I’ve seen a man who does what he really wants, what his heart tells him! I think retirement and the determination of mature age contribute the most to this. Anyway, in terms of clothing and aesthetics i fully identify with the suit and its accessories, as well as with the A2 jacket and the blue flannel pants. Congratulations Mr Ian, trully an impressive presentation!


One of the loveliest of these.


My kind of guy. I think as a man gets older it’s more important to dress well, not less. I’m retired, and I wear my nice clothes all the time. Why wait for the moths to eat them? The other thing that comes through here is the reminder that all of this is supposed to be fun.


Really enjoyed this read and also thought the investment advice was spot on!!!

It’s great to see somebody whom is learning within their own parameters of style which they have been living over their lifetime. In other words, he didn’t make some money and then try to become someone else.

Dr Peter

Magnificent! I like Ian’s attitude and I like his style. The approach he takes towards clothes is rather similar to mine. I loved reading this piece, Simon. It’s great to see people like Ian be presented (if that’s the right word) in your blog. Thank you.


Good evening..Ian seems to be a man who enjoys life..Ian keep it up and stop…much joy to you all…peace


Excuse me..I meant to say don’t stop…cheers


“Be yourself, everyone else is taken”
A wonderful article about a wonderful man. One of your best.


Wonderful profile. He also looks natural wearing a hat, unlike most menswear shots.


Hi. Something I forgot to mention in my earlier comment, in addition to a more senior person (I’m 67), it’s great to see someone who not in menswear or the creative arts etc. I remember mentioning in a comment years ago it would be good to have people from more regular backgrounds-plumbers, builders,, nurses, and in this case train drivers and the like. Your readership may be more diverse in the very broadly st sense including employment, than perhaps previously thought.

Tim Jackson



Hi Simon. So much to like and so elegant. A lovely deep shirt collar goes well with this suit style, and the pale tone of the hat compliments a similar colour in the tie.


Fantastic looks, especially nice to see an Eastman, Trickers, and Sun Surf featured. I’m a big fan.



Just shows that a great personality and style go hand in hand. How nice to read about Ian.


Where is the bracelet from?


A pawn shop in Essex Road.


Lovely post! Ian looks best in outfit 3 IMHO. It just somehow seems ‘him’ naturally. It was good to read his CV in the profile. I liked that he wasn’t an “Oxbridge to the City” kinda guy and shows the reach that Permanent Style has.


Love this article!
And nice to see someone appreciate a vest/singlet as much as I do (vest and overshirt has been a staple of my wardrobe for the last 20 years now, just the style and aesthetic has matured as I have).

I’ve never understood why vests never come up in menswear conversations, especially when it’s so difficult to find decent quality ones rather than, as Ian points out, cheap badly made stuff from the high street that warps and frays after about 6 months.

I thank Ian for the recommendation to check out Henri and wonder if he has any further advice buying from them? The sizing on their website seems somewhat enigmatic!
And if anyone else has any recommendations for good quality, ethically made vests with a good fit, then please jump in 🙂


The vest/tank top/”wife beater” definitely comes with associations – I associate them either with an older man with issues suffering from drinking and anger management issues (usually taken out on his spouse or offspring), or as something wrong by gymbros to show off their gains. Rather dreadful associations when you think about it, and reeks of classicism, but it is what it is.

I still ended up getting a ribbed vest this summer, after reading a post Derek Guy made about using them for layering during summer. I wear it with denim, suede chukkas and overshirts. The negative associations can play well with a rougher, possibly slightly sleezy look, if you’re that type.


Thanks for the nice comments! I’m a 38-40 chest, which usually equates to small or medium in t-shirts. I find a size 5 in the Henri vests fits me perfectly. I hope that gives you a bit of guidance.


Thanks Ian – that is incredibly helpful, especially since I’m roughly the same in the chest myself. Thank you!

@Simon & @Sam – it’s an interesting point you both raise on associations with wearing a vest, albeit from different ends of the spectrum. I wonder if geography has anything to do with that? As a teenager growing up in the East Midlands, a vest with skinny jeans and winkle pickers with a cheap cardi on top was the go to for me and pretty much all my mates (rather than old-mannish as Simon suggests, this was definitely a self-consciously “sleazy” look, as Sam describes – but that felt right when we were all gobby teenagers and it was cheaper than buying a Fred Perry polo just to get the collar off, which was another favourite look). Nowadays my go-to casual outfit is high rise chinos and loafers with a vest and something like a cotton twill, linen or denim shirt over the top (not unlike Ian’s second outfit above I suppose, just with less patterns usually). The advantage I find with this is that by buttoning up and tucking in the shirt, I can quickly make my outfit formal enough for most occasions that don’t require a suit.

Perhaps the “sleazy” association is still there and my colleagues are all waiting for me to start to drink White Lighting and get frightening. Or perhaps I am drifting into the realms of being an old man before my time. I suppose I should aim to be conscious of the association of clothes with others. Ultimately though, I’m always very comfortable (both physically and in terms of identity) in my go-to get up, and that’s probably one of the most important things for me when it comes to picking my outfit


Hey Simon, long time reader, first time poster.
I’m a Yank but happened to be in London two weekends ago, and found myself in The Blue Posts listening to some really good blues upstairs. I looked across the room and saw this cool older gentleman wearing a characterful outfit and thought, “what, isn’t that the dude from that recent PS article?” I pulled this article up and walked over and said, “excuse me, but this is you, isn’t it?”
“Yeah that’s me!” Said Ian.
Really fun to run into him, and just wanted to say it is great that you’ve created this little community.
Love these reader profiles, please keep them up.