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Simon is only our second reader profile from outside the UK. He lives in New York, although when we talk on the phone he’s actually in Washington DC, having just landed on the red eye from Arizona. 

Simon travels a lot. He’s a journalist and his travels drive a lot of his wardrobe, which has to be practical off camera but also presentable on it. Although this can be restrictive, it’s also introduced him to many little shops and brands, from Miami to Belfast.

Having met at our pop-up shop in New York last year, it was great to have the time to talk to Simon more - about his time as a DJ, about menswear silhouettes, and about comfortable shoes for the (slightly) older man.

Outfit 1: 

  • Jumper: The Real McCoy’s
  • Linen knit shirt: The Real McCoy’s
  • Socks: Rototo
  • Trousers: P44s, The Real McCoy’s
  • Trainers: New Balance

Tell us about the kind of journalism you do, Simon.

Well I worked for many years in the UK for Panorama, as an investigative reporter. After that I was the current affairs correspondent on The One Show for a white. And now I work for Al Jazeera in the US - I’m the senior reporter on the investigation team. So a lot of moving around, a lot of interviews. 

Can you wear clothes like the ones pictured on the job? 

The casual pieces like this first outfit, sure. The job has two phases really: on screen and off screen. During the off-screen part I can wear what I want, things that are very me. 

I can’t wear clothes that take too much preparation - shirts that need ironing, trousers that need pressing - because it’s just not practical. But I dress in very functional clothes anyway, so it’s easy. I’d wear the outfit shown here for a coffee in the morning in New York, but also yesterday walking around in Arizona. 

And when you’re on screen?

If I know I’ll be doing interviews on screen, or a stand up, then I’ll wear something smarter - but also that doesn’t stand out. I think most journalists would agree that the aim with your clothing there is to not distract from anything you’re saying. 

I remember in the days when I was doing The One Show - where it would be two days of travelling, two days of shooting on screen - I drifted into a kind of Ivy League look: chinos, button-down shirt, jumper. It was anonymous. The shirt would have been OrSlow, the jumper from Scotland, but it would be very simple.

The clothes you’re wearing here are a little more characterful than that, though. 

True, and sometimes I might tone it down a little. Yesterday I was wearing these same Margaret Howell trousers with just a navy jumper and some Alden loafers, for example. 

But actually I find as I get older - I’m turning 50 this year - I can wear more interesting things. I think if I’d worn white trousers like this 20 years ago, it would have been seen as more of a fashion choice, but it doesn’t now. Part of it might be that I’m just more comfortable in those clothes - they are very much me, they suit who I am, and I’m used to them. 

Are the trainers part of that journey too? 

Yes, partly. I used to wear Converse all the time - high tops, low tops, with everything. But walking around New York all day I eventually felt the effect of having no support at all - it was killing my back. 

And these felt like a good compromise - they’re not the hyper-cool trainer that an ad exec wears, to try and look down with the kids. But they’re not the old person’s comfort-is-everything trainer either: the kind of thing a politician wears to a conference.

Outfit 2

  • Flannel suit: Drake’s
  • Denim shirt: Vintage, from Front General
  • Undershirt: Vintage, from Front General
  • Pocket handkerchief: RRL
  • Socks: Drake’s
  • Shoes: Black-scotchgrain longwings, Alden

How did you get into more classic, crafted menswear?

That was a function of travel. My work has meant that I’ve lived in DC, Belfast, travelled almost everywhere around the world. And in each place I found different styles, was exposed to new things. 

I remember walking into The Bureau in Belfast, and seeing a raft of brands I hadn’t seen anywhere else. Then Oi Polloi in Manchester. In Florence I discovered vintage places, and little menswear shops that you couldn’t buy anywhere else. This was partly before social media too, pre-2010 or so, when there was much less awareness.

I remember when I first found your website, I was surprised that everyone knew about these brands - that it was a much bigger world than I’d realised. 

Do you still seek out these kinds of places when you travel?

Yes, absolutely. The great thing about the internet is that now when I know I’m travelling somewhere, I’ll look up whether there’s a nice little vintage shop I can visit. 

So there’s a great vintage shop in Denver I went to as part of a work trip for example - La Lovely I think it’s called. There’s Supply & Advise in Miami, that’s great. And when I lived in Brooklyn I’d go to Front General, where this shirt and undershirt are from. 

Last year I went to Tokyo for the fifteenth time, and no matter how many times I go there I always discover something new - some cities are just built like that, so big and so set up for small retail. 

This second outfit is smarter - is this the kind of thing you wear today when you’re on screen? 

Smarter than this really - this Drake’s suit but with a shirt and tie. Although, wearing a tie on TV now almost seems like too much: because so few people wear them, wearing one might stand out more than not wearing one. 

I wear this suit with a tie when I’m giving speeches at conferences though, and the night before these shots were taken I wore it to an awards ceremony in New York, with the same denim shirt and handkerchief, because you can be a little bit more expressive there. 

Outfit 3:

  • M65 field jacket: Vintage, The Vintage Showroom
  • Trousers: Margaret Howell painter trousers 
  • Beanie: Drake’s
  • Jumper: Margaret Howell
  • Boots: Alden Indy boots
  • Bag: Vintage

The M65 here looks great, where was it from? 

From The Vintage Showroom in London, back when they had the store. So much of my knowledge about clothes comes from talking to managers of vintage stores, who 99% of the time are incredibly helpful and friendly. 

I actually got stuck in London during Covid, and The Vintage Showroom was one of the only shops that was open. It was about 100 metres from the Air BnB where I was staying, so I used to pop in most mornings and just have a chat. 

They had a first model M65 and I’d always wanted one. It’s hard for me to find vintage though, being a bigger guy. Everything is always too small. So when I tried this one and it fit perfectly, it was a done deal, no brainer. I love vintage sweatshirts too, but during their 50 years of existence they’ve all been washed a thousand times, and now they’re all tiny. 

How did you get into vintage clothing?

My interest has come and gone over the years. The first time was probably when I was growing up in the mid-eighties: the fashion was Lacoste and Lyle & Scott knits, with Sta Prest trousers, but a lot of people would seek out earlier, unusual versions of the knits in bright, lurid colours.

Then when I was 18 and 19, I was DJ’ing and the music was funk, Northern Soul. Everyone there would dress in vintage from the fifties. They’d wear white-collar shirts, vests, leather jackets, all from vintage markets around London. I didn’t wear most of it because it felt like costume to me when it was all together, but I saw it and appreciated it, and adopted the odd piece. 

In my twenties vintage wasn’t really consideration, it was new brands - Ralph Lauren, Calvin Klein - and I was working too hard to really think about clothing much. But then vintage came back around in my thirties, just because I saw more people wearing it, things you couldn’t get in normal shops. 

I vividly remember seeing this older guy sitting on a bench in New York, wearing an amazing, thick suede overshirt with a red beanie. It looked about 100 years old. I tried to find something similar everywhere, but without any luck. 

I have been eyeing one in Drake’s, but it’s $2000! Maybe one of these days. With the red beanie that would certainly be a very current look.  

It sounds like you’ve honed your taste over the years. 

Yeah, I think when I was younger I would be very influenced by every shop I went into - it would be about trying to wear what they were offering. Today I have a much clearer idea of what I like and what suits me, so it’s more a case of going into a shop and seeing what interesting things work with that. 

Is the bag vintage as well? 

Yes. A while ago I went to Brimfield, this big antiques market upstate. I didn’t find anything there, but on the way back I dropped into a vintage shop in Sag Harbour, on Long Island, and found this great old bag. 

Do you think you suit bigger pieces like that, as a bigger guy?

I never thought about it actually, but you’re probably right. People do comment that it’s the biggest bag like that they’ve seen, but it never feels big to me - probably because of my height. I need to repair it actually, I’ve done that a few times with an old pilot’s bag of mine, and this needs some attention too.

It also reminds me of a benefit I find in sites like yours: explaining why things work and don’t. I don’t read guides to learn how to dress, but now and again one of them will explain something well. In this case, it reminds me of a point I read that clothes are a lot about silhouette - this scale of bag works with the silhouette of my shape and the kind of clothes I wear. 

I remember years ago I bought a big Stetson hat, and thought I looked a million dollars in it. I wore it in LA - carrying it on my lap on the plane from New York. But when I walked into a bar I saw another guy wearing one too, and it looked so much better on him - a billion dollars! I realised the proportions just didn’t work on me. 

It now sits on top of a wardrobe in my house, and makes a great ornament. 

Thanks Simon, a pleasure and hopefully see you in New York in the Autumn. 

Sounds great Simon, looking forward to it.

Photography: Christopher Fenimore

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Lindsay McKee

Just like the “How to dress like” series of posts, I just love these reader profiles, and then wondering who’ll be next!!!


Good Monday morning…as stated this gentleman is a journalist..he is wearing his style…good for him….peace


A very nice read about how to be stylish and also not compromising on comfort at the same time.

Peter Hall

I recognise the need for smart,stylish comfort and avoiding tight clothing as I’ve aged. As mentioned by Simon, Ivy works well here, and then go have fun with outerwear and scarves. Luckily,by the mid 50s your have quite a deep sense of self – underpinned by experience .

I have also returned to wearing much more white/ecru trousers and jeans.
Love the shade of the Drake’s suit.


These reader profiles remind me so much of the brilliant Mr Porter “How I dress” videos (PS videos of reader profiles …. now there’s an idea !”)

The flannel suit with the denim shirt looks amazing but the other looks aren’t necessarily to my taste.
However , seeing the other looks makes me appreciate that when it comes to casual clothing there are no rules .

I note the Margaret Howell trousers . Never heard of those so good to learn about them . Unfortunately the price is eye-wateringly expensive !


Hi Simon,
Do you mind sharing where in London the sales shop is located? I tried to look it up on their website, but it was not clearly identified amongst the ~5 London stores listed there.
Thank you.


Flannel suits are very popular this winter which, in London, feels colder and longer. However, wearing a denim shirt would not be acceptable in my office. My colleagues would call me an attention-seeker. I’d choose a plain Royal Oxford shirt and grenadine tie instead.

Drake’s suits have patch pockets which are, for me, too casual for business. The price has risen to £1.680 (£1,195 for the jacket and £495 for trousers) which is eye-wateringly expensive for a half-canvassed suit. Bizarrely, the tailoring part of Drake’s website now puts the jackets under “blazers” and the suit trousers in their own separate section.

For comparison, Anglo Italian’s flannel suits are fully canvassed and only £1.450. Their MTO jackets, also fully canvased, are a reasonable £990, same as Drake’s half-canvassed RTW jackets. In terms of value-for-money, those are big differences as both brands use Italian factories. I would now only consider buying Drake’s Archive sales but the last one had very limited stock.


I liked this a lot, out of all the reader profiles maybe the closet to how I dress. As a larger guy myself I agree vintage can be difficult to find and I would very much like a first pattern M65 so pretty jealous of Simon’s

Gary Mitchell

Well, there is no denying that it/he looks comfortable.

Matthew V

Very enjoyable article. I can relate to the interest in music, plus also embracing seemingly everything new from days influenced by casuals in the 80s, then all the new and wonderful shops in London, Nottingham, on travels abroad etc (albeit often with an eye to Mod culture). Then in forties and now fifties settling into what I really enjoy wearing.
I have purchased from Supply and Advise, online, would like to see it in person, seems very well curated. I can also relate to the obsession in finding the perfect M65 jacket, judging my the several I already own! I remember my first, from Silvermans in Mile End, bought when I was about 16 and in the Air Cadets, wish I had kept it.


Hi Simon and Simon,
I really enjoyed this post. Simon’s look nicely marry style and practicality. Being an older man, comfortable footwear really resonates with me. Great cardigan from the Real McCoys, I have one in dark grey and whilst a bit expensive it does get lot of use and the M65 looks great – I impatiently await the Vintage Showroom either reopening or their online restocking, but may have to now go the Real McCoys route.
Finally one for Simon C, I always find these interviews enjoyable and interesting , especially as the people have such a wide range of backgrounds and occupations therefore being more relatable rather the more contrived interviews elsewhere where everyone is in fashion, marketing, architecture or some form of ‘activist’ etc.
Perhaps someone in the construction (or more manual) industry at some point?
Thanks again for providing an interesting experience over coffee three times a week.

Peter Hall

I too have always considered an early M65 a very desirable find.

I wonder if I should stop searching anf just buy a Filson field jacket.


If I remember correctly, there is a PS article on Peter Zottolo (urbancomposition on IG), who is an electrician by trade, in which he talks about clothes used for manual labour.


Hi Simon, Simon sounds like an interesting chap. I have to say that for me, the first look is perhaps a little ‘young’ for him. I generally don’t agree that one should dress according to age and would argue people should wear what they like but something in this look jars with me slightly. Its perhaps reminiscent of the street wear guys you see on Instagram posting endless ‘fit pics’ who are generally somewhat younger than your featured reader.
I love the fact he unashamedly dresses for what works for his lifestyle. This honesty is refreshing. Very often i feel the classic menswear fan dresses in a manner unsuited to his situation or occupation. This is understandable as you may like certain clothes or looks and want to wear them but my can it look unnatural.


You look great and interesting conversation given your background. Thanks!


Simon is an interesting man and given his profession it’s understandable why he requires practical clothing. So, I really like the M65 jacket and the flannel suit as examples of practical and versatile travel clothing. However, certain outfits I don’t care for, particularly #1. Cargo pants and tennis shoes is a teenage look that simply looks silly on a grown man, particularly an older one. The denim shirt with the flannel suit is a head scratcher quite frankly and just odd looking.


Another great article – thank you Simon and Simon. The style is great and I’d wear all of it (and do in some cases). That M65 looks to be in phenomenal condition – excellent find. Keep rocking it Simon – from one large nearly 50 year old to another!


Hi Simon
We’re the same age, I’m also about to hit 50 this year and I can completely relate to your sentiments about comfort!
The M65 has had a lot of love in the comments! I smiled when I saw your M65 outfit because I also have the very same first iteration of the jacket from The Real McCoy’s, great outfit by the way. I used to have one as a student that’s now lost, but I’m really not fond of vintage clothing so I bought one new that I could hopefully put my own stamp through use. Absolutely superb quality of materials and craftsmanship from McCoy’s.

Jim Bainbridge

I like the denim shirt – looks like it has aged nicely, and it’s not *too* heavy (as lovely as heavy denims are, they can look a bit out of place with tailoring). And while for some, trainers/sneakers will never be palatable, I think this is a good way to wear them; and in general, this is clothing thoughtfully chosen to fit a lifestyle. Enjoyable to see and read about.
P.S. that shot of a turnup sitting neatly atop the shoe with just the right amount of green sock peeking out is just so pleasing.


These reader profiles are fun, and I particularly liked this one, but I find them all quite derivative and rooted to the same themes and brands…in particular Alden, Drakes, Alden, Drakes, Alden, Drakes…rinse repeat…

Simon G

Hi Simon,

Great article. By Simon, about Simon, and for a Simon (not exclusively).




I’ve been looking out for a M65 jacket for quite a while too, without success. I’m a hobbyist photographer and the utility of the pockets really appeals to me. I therefore appreciate how others are wearing this jacket.
On a separate note, Simon refers to himself as a “bigger” chap. That’s hard to tell from the photos. I’m guessing he must be quite tall. Just out of interest, what is his height?


Nice to see a man so well-dressed and comfortable in his own skin! I think all outfits have harmonious proportions, color combinations and intriguing texture. Very wearable. I am 20 years his junior and would like to wear everything just like that. And, although I do love loafers, it feels good to see someone wearing a shoe with laces every once in while.


A bit late joining the discussion here from New York but having recently expanded my vintage military wardrobe (thanks PS!), I’ve found that both Broadwayandsons.com in Sweden and armynavywarehouse.com near Dallas, Texas to be outstanding sources of M65-type clothing. The former has outstanding service and the latter a wide selection, both with very reasonable pricing.

Simon Chambers

Very interesting to see another 50 year old Simon who travels a lot for work. Mine is in humanitarian response and global advocacy, but I resonate with a lot of Simon’s issues in travel, the issues of having clothes look good when you get there, and needing to dress for different parts of your work.

Triple monks

He has a good eye for color. He also has the style of someone who wasn’t dressed by the internet, if that makes sense.. The indigo blue RRL pocket square was a nice individual touch.
Probably the best dressed person in the reader profile series. He manages to dress in a way that points in reference to menswear without being overbearing. There also aren’t really any #menswear cliches in these looks either.
We need more people like this featured in the future!


Nice guy, nice looks.
i really like the McCoys linen knit, but can’t get past the top button only fastened look. It makes me think Simon has a bit of a spare tire, which from the other pictures he plainly hasn’t.

Triple monks

The look has been done since the 16th Century, if not before then. There’s a precedent…

Triple monks

But your right, it isn’t the most flattering of looks

Ben frankel

You either got or you haven’t got style- and sung by Sinatra.
Simon has style. Terrific read, and faultless content, thank you – both Simons.


Couple of great ones recently. The Emilie Hawtin was fantastic. How to dress for your figure and (I’d guess, based on her prose and her photos) her personality. My wife would look daft dressed in Emilie’s wardrobe. Just as I’d look daft in a soft-shouldered suit (doesn’t work for my figure – sloping shoulder bones and a reasonably deep chest – I played waterpolo for my university – need the opposite) or a bomber jacket (I’m in my 40s apart from anything else). Yet Emilie looks fab. And played to the gallery with her suggestion men should be encouraged to wear suits, of course.
This too is the same thing. Love the flannel suit and the blue. (Suit doesn’t fit well. We get that. Probably why you took the photos the way you did. Pocket-square and two pockets on the shirt – come on. Green socks?! And yet, and yet.)
If only he didn’t wear a Rolex. Why would anybody do that? Folk call it ‘working-class aspirational’. That isn’t an insult on the working classes as it may seem to outsiders (goodness, I know that – I’m half immigrant and my mother was a nurse) – it’s more of a striving to something you don’t understand sort of thing. Like joining Soho House: join White’s or the NLC if you like, drink a pint at the club attached to the church, get pissed at the pub on the corner, snort coke from a bald man’s head – or a dirty toilet – all of these can be an expression of personality – but Soho House, Rolex and Omega are an expression of a desire for somebody else’s personality. As repulsive as a Louis Vuitton handbag.
Did you read Robert Armstrong’s recent piece? He was very good on what sort of clothes suit different figures. Also, even though US-based, he’s a bit closer to what the financial guys are wearing (and everybody else follows us a bit later – let’s call it middle-class-aspirational – but it isn’t really, bankers dress up to convince their bosses they’re serious, lawyers and accountants follow their clients, and other folk follow with a lag – financial folk are cynical rather than aspirational in their dress). He was talking about tailored clothing. Not in a vintage or ironic kind of a way – even in the US, the bellwethers know winter’s coming and that means more beautiful clothing and more manly shapes (perverse as it seems).
Are there more articles from women coming up? Seems to me that most women (perhaps with a closer eye on winter) prefer men in suits: is that something that can be proved or disproved? And maybe a discussion on what men are dressing for – career progression, male-peer-group approval, feeling good in the mirror, attracting women – would be interesting. Especially if they could be contrasted (if most 30yr old men dress for women – I did – and think women like leather bomber jackets – but most 30yr old women want a man to wear a jacket and tie – you could start a revolution in menswear). It seems to me that you now have the scale to approach the folk who could answer these questions: you’d want a women’s magazine for part of it – do you have it, would it be fun?


Hi Simon,

Reprimand taken. Shall douse my rhetoric, soften my polemical style and temper my prose. You’re quite right, I wouldn’t make a Castiglione.

But I do wonder whether a site such as this should warn people about the strong negative associations that certain brands have.

I’ve heard managers bawl out the juniors – you cannot wear that to this meeting – you’re not supposed to be a chav-made-good, you’re not a #### estate agent etc. The junior, who may have spent a month’s rent on the item and felt rather good about it, blushes horribly. In person, I’m rather softer, but do have to have such conversations. ‘Looks lovely, but some clients have odd hang-ups, some may think a XXX is a sign that you…’ Seems harsh. But I know one wimpish manager who doesn’t have these conversations and simply leaves those who dress oddly (beautiful reddish shoes, a suit that a popstar could wear on a red-carpet) behind. Isn’t a hard word the better route? And isn’t it nicer to get it on a site like this, in the privacy of the internet, rather than on the floor? (And, in a perfect world, before you’d dropped a few grand on a watch or a jacket or some shoes that simply can’t be worn in the context you’d imagined.)

(When I first joined the industry, I spent what I thought was a fortune on a black ready-to-wear Aquascutum suit – I loved it, and wore it with a Tie-Rack woven silk tie – should have been obvious to me that a black suit wasn’t the thing – it wasn’t obvious at the time – I was bawled out – glad of it in retrospect, only in retrospect – but there are subtler things, I now realise. And also things that would have seemed subtle, or I would have deemed unimportant, when I was 25 but now seem like glaring danger signs. Utterly unacceptable. You’ve had something of the same journey in a different and maybe softer context, I feel – no, you can’t get away with a fedora and the Sexton coat and the collar turned up and turn-ups and suede shoes!)

Incidentally, if I’m trading article ideas with you, it struck me that there may be something on status dressing and appropriateness. Also an ugly subject. I have a lovely bespoke double-breasted jacket. It’s a bit dramatic (not Edward Sexton, but it might as well be). It’s outerwear, and I think you can get away with a bit more in that (especially if you’re willing to fold it up in a reception area). But, as I’ve said, I’m in my 40s. If a 20-something wore something like that to the office, I’d advise him against it. It would be completely inappropriate for him.

I’m not entirely sure I can explain why. Or possibly (certainly) I can explain why, but not in a way that makes me seem anything other than a monster. And yet kids – dazzled by their first bonus and keen to make an impression on their bosses (as I’ve said, bankers are cynical in their dress), probably need to understand that nuance. The thoughtful among them will do some research. I expect many will end up on this site. How do you explain that a moderately successful man in middle-age gets to wear one thing while somebody starting out, who may be (and this, of course, is part of it) lithe, sexy, young and generally more in keeping with what the ads show simply can’t wear it and has to be a bit dowdier? As I said, it’s ugly but it’s rather important if one of the aims of dressing is to get ahead. (I vaguely recall some French author – maybe it was Stendhal, I can’t find the passages – dealing with this sort of thing.)

Looked at the link you gave. Thank you. Unconvinced that they were saying that they liked T-shirt and jeans. Simple and unfussy, yes. But the simplest of styles that they advocated was tailored linen trousers and a polo-shirt. I like linen trousers and polo-shirts, can’t stand jeans (Jeremy Clarkson or the Marlboro Man) and think T-shirts unattractive unless you’re James Dean. Definitely support more articles by women making their nuanced thoughts known – even if it’s a bit late for me!

Hope I’ve softened my rhetoric sufficiently without being entirely insipid. All the best, John

Simon K

This exchange got me thinking about getting female attention. I just interviewed my wife at the breakfast table. She was of course against the idea of generalizing but getting that out of the way the supreme top priority was clear: Cleanliness
As she put it giving your finger nails some extra care beats that new suit. Also, it seems men often underestimate the importance of smell.
Below these priorities it turns into different niches, what I understand. Meaning different style preferentials? Some like status brands, some like functional materials.,
Then she expanded to the value of coming out as complete. That everything is in line. As an example ethical consumption and style seems to be a big thing in Stockholm. If you want to come out as sympathetic you then cannot talk nicely about the environement while having clothes that are not ethically made. What that means I do not know since she had to run for the metro.

Simon K

I really liked your article on hair and beard care.I want to get good personal, impartial advice. As you bring up it is not that easy. My hairdressers normally say that this or that cut is popular today. It is not quite what I need to know. Also, how to not end up looking and feeling to fussy. Most of us want to feel and look at home in different settings. Simon in this Reader Profile touched on that in the role of the reporter.

A. B.

I wouldn’t necessarily say that everyone follows the finance/law guys in style/fashion. Different work fields dictate different tastes/styles; for example, the creative crowd would never, ever, dress like a lawyer. And Simon here, being a journalist, is another example: menswear is not spearheaded by one particular group.