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