Pedro is a reader in New York – one I’ve known to say hello to, but never really had a long conversation with. It was lovely doing so a couple of weeks ago. He’s thoughtful about clothes and his relationship to them, self-aware yet also a real menswear guy in terms of knowledge and research.

We talked about his family in Puerto Rico and how their approach to clothing affected him growing up – plus what his mum thinks about his Sagans when he goes back! He’s also definitely the only reader to have told me Permanent Style reminds him of Roland Barthes. 

I hope, as ever, that you enjoy the conversation and find it both interesting and useful. A quick search can bring up the rest of the reader profiles if you want more.  

Outfit 1

• Suede overshirt: Drake’s/Hodinkee
• Cotton overshirt: 18 East
• Jeans: J Crew
• T-shirt: Lady White
• Boots: RM WIlliams
• Cap: Western Hydrodynamic Research
• Sunglasses: Lesca

What do you do for a living Pedro?

I work at Hodinkee, selling watch and jewellery insurance. But I come from a film and video background – I studied it at grad school and one of my favourite previous jobs was transferring Super-8 and 16mm film to digital. 

I came to New York hoping to be an artist I guess, but there’s a connection there with watches, in that the relationship between analogue and digital always fascinated me. Even though my career has changed quite a bit in the past 15 years, I think that’s carried over. 

What did you do when you first came to New York?

I worked in a restaurant to earn money while I was doing other film jobs. The pizzeria I worked at is where I met my wife, who’s now a full-time photographer. Eventually the needs of a modern life caught up with me though and I needed to earn more – I’m 40 next year, and we have a three-year-old son. 

When did you first get into clothes? 

That’s hard to say, it’s been a while. But certainly I started looking into it more in the 2000s, back when silhouettes were much slimmer! I remember going back to Puerto Rico to see my parents around 2004, when I was still in college, and finding this amazing suit in a department store called Marshalls. 

I think I talked about this once on Permanent Style actually. The suit was a tweed three-piece from Ralph Lauren Purple Label, grey herringbone with a subtle purple overcheck. It had patch pockets, swelled seams, and was reduced to something like $99. 

It looked so cool, and I remember saying to my mum it was what I wanted for Christmas. She didn’t believe I’d wear it, but it did so well – I wore all three pieces separately, the jacket with slim selvedge denim and black Converse, that kind of thing. I wore the hell out of it for 10 years. 

When did you start spending more money on clothing, and tailoring in particular?

That was when I got married, in 2017. J Crew was the main place, for their clothes but also they had brands I got into like Alden, Red Wing. Though I was never really a big Red Wing guy; RM Williams was more my chunky boot. 

In fact there’s a specific origin story there. When I was in a film class in college – in Appalachian State in North Carolina – we had this professor called Leon Lewis. He grew up in the seventies and was originally from Buffalo, New York. He was a great beatnik character. 

You could always hear him coming to class because he wore these RM Williams that clip-clapped down the corridor. He wore perfectly fitting jeans with a crease down the middle, tortoiseshell glasses, a little moustache and a kind of weird mullet thing. It sounds odd but trust me he pulled it off.

So he got you into RM Williams?

Yes and I remember him talking about them actually. He boasted that he walked 20 blocks in New York City one day in the rain, in these leather-soled Goodyear-welted shoes, and no water got in. I’m not entirely sure that’s true, but the way the boots embodied how he projected himself really stayed with me. 

As I get older I think about these things more – about how I want to project myself. I’d like to be someone that clearly cares about finer things but isn’t too stuffy about it.

What are you wearing in this first outfit? 

So that’s the Drake’s suede chore they did with Hodinkee, worn over an 18 East overshirt and a white tee from Lady White Co. Lady White are my T-shirt of choice at this point, they’re good quality, don’t shrink, and are very consistent from season to season.

18 East is a company I really appreciate for their fabric choices, but the style is more streetwear generally. I saw this overshirt on a colleague though and I thought the style and the fit was very wearable. 

And what is Western Hydrodynamic Research? Sounds like a biolab!

Ah, yeah it’s this surf company from California, they’ve done a few collaborations with streetwear brands, the name is a reference to surfing I guess. I liked the five panel construction with that little pinch at the top, it felt rather vintage. 

Outfit 2

• Jacket: Proper Cloth
• Shirt: Wythe
• Trousers: Natalino
• Shoes: Berwick
• Sunglasses: Lesca
• Sweater: J Crew
• Watch: Serica

You mentioned your family are from Puerto Rico. What was clothing like there, was your Dad an inspiration?

Yes my interest in clothes definitely owes a lot to my parents. My father’s a banker and when I was younger he wore a suit every day. Now he wears separate pants, maybe a crisp white shirt; in Puerto Rico you don’t need a blazer or suit necessarily, but he’d put one on for a meeting etc. 

When I was younger he always looked great: high-waisted trousers, pleats on everything, but also loafers without socks. He’d take me to Joseph A Bank and buy Cole Haan loafers, that kind of thing, and I’d think they looked great. 

My parents tease me about it today, but it all came from them. They love to get dressed up. I’m not sure if it’s a Puerto Rican thing or a Hispanic thing, but people there definitely like to dress up for an occasion – not necessarily formal, but just look nice for going out for a cocktail, or for a meal with their family. 

That’s certainly something that seems to have been lost culturally in a lot of places. 

Absolutely. I think a lot of it is around events – it was certainly a Roman Catholic thing, as we would all go to church on Saturdays, all dressed up for that, and then either go our or come home. But even at home it was an event, all of us around the table. I have very fond memories of that. 

Do you overdress a little, maybe reaching for that kind of thing?

Like a lot of menswear guys I guess. I’ll ask my mum when I’m coming back to Puerto Rico whether I can wear a double-breasted blazer to something and she’ll say no, that would look odd. And when I go out with my wife, I like to get dressed up and she has to rein me in, saying we’re not going to a gala!

It’s definitely a case of looking in the mirror before I go out and thinking what’s one thing I can take off, that I don’t need. 

Where is this jacket from?

The jacket was from Proper Cloth, the first thing they made for me. It’s wool and linen; I thought it would be a kind of summer tweed, but it ended up a little heavier than I expected, so I wear it more in spring and autumn. It’s nice, breathable and with some good natural stretch.

My only regret there is I didn’t make the lapels wider, which I didn’t realise I could do at the time. They’re still good, three-and-a-half inches I think, but I’d like them wider.

And you’re a pretty broad-chested guy, so three-and-a-half inches is less on you proportionally.

Yeah, true. Then I’m wearing a Wythe chambray shirt and trousers from Natalino – they fit me really well. The tote bag is an LL Bean and the watch is from Serica. I got my first Serica in 2019, after having vintage Seikos in the past but getting frustrated at vintage, the time and cost of looking after it.

I liked the fact the Serica was manual wound, I like that connection to the mechanism. They’re all automatic now.

Outfit 3

• Jacket: Drake’s 
• Shirt: Wythe
• Jeans: J Crew
• Shoes: Berwick
• Belt: Velasca
• Sunglasses: Lesca

What do you wear for work?

I work from home quite a lot, but make sure I go into the office two or three days a week. At home I wear leather slippers, jeans or drawstring trousers in like a heavy cotton from this US company called Battenwear. 

Then I’ll wear a T-shirt, an overshirt, and put on some Belgian loafers if I’m going out. I’m perfectly comfortable doing that. Although this relaxed look can definitely go too far – I remember once going out to the neighbourhood in a Camber hoodie and sweatpants, and it felt so odd, like wearing my pyjamas outside. 

It was around the time Aimé Leon Dore started becoming big and their ads were so good, with that look and New Balance. It made me think about it again, want to experiment, but no it did not work for me.

Do you wear a lot of Belgians?

I do now, yes. I used to wear loafers a lot but I’ve gradually switched. The first ones I had were from Crown Northampton, I couldn’t ever stretch to the original Belgian Loafers. But then Baudoin & Lange came out with their ones and they were a bit more accessible. And I have since bought Berwicks – those are my default now – as well as Yanko. 

I wear them all the time, even when I go back to Puerto Rico – my mother asked what they were the first time and I was like ‘they’re Belgian loafers – Dad wears loafers, they’re just like them’. My wife doesn’t mind them, but she definitely thinks I have too many at this point! 

Berwick is sold through the UK site A Fine Pair of Shoes. They’re great value, with a good leather/rubber sole that I’ve found is very resilient. Yanko is another Spanish brand, and probably made in the same factory – they have the same codes inside. 

Unfortunately I fell over in the Yanko once and thrashed the outside of them, taking off a lot of that top layer of deerskin. Fortunately I seem to have brought them back to something decent with Saphir Renovateur. 

So this outfit with the Belgians is pretty typical?

Yes, those are the Berwicks, worn with a Drake’s Games Blazer, a chambray shirt from Wythe and jeans from J Crew. The chambrays from Wythe fit me perfectly in large, even the sleeve length, so I have several of them. Once you get something that really works for you, it’s worth having a few. 

I like the combination with all the blues – is that a common combination for you?

Yeah it’s pretty common. Before I got into menswear I was very much a navy-blue kind of guy, and I don’t wear black that often, so blues work well. It’s nice to do something a bit more interesting and have different shades. This is the kind of outfit you could wear anywhere in New York City and not feel underdressed or overdressed. 

I know the Instagram account you run, Studied Carelessness – is that just a personal account for outfits and things, or are you trying to do something different with it?

It started it in 2018. I actually had an Instagram account before that was little videos based on two artistic ideas: Kino-Eye, from the film director Dziga Vertov, and Readymade, from the artist Marcel Duchamp. I called it Kino-made. It was films about that idea of living in a ready-made environment. 

Anyway, that didn’t really take off, but I’ve always been interested in the theory. In fact some of the inspiration came from the French writer and photographer Roland Barthes as well, and I think Permanent Style has done something like that – taken an academic approach to clothing but in a contemporary way. 

The problem with Style Forum and other sites is that they’re rarely looking forward, only to the past, and so they become archaic and then costumey. You don’t want to step out of your house in New York in 2024 and look like a character from a Dickens novel. You want to look like a contemporary person, just one who knows clothes and has his own sense of identity.  

Pedro is @studied.carelessness on Instagram

He also occasionally writes on his Substack