Conversations New York

Words of Wisdom with Josh Peskowitz

By Drake's

Apr 6, 2023

Words of Wisdom with Josh Peskowitz

“Whaddya wanna know? I’m an open book?” And there begins our conversation with Josh Peskowitz. He’s written, he’s styled, he’s designed, he’s led department stores, opened up his own shop and shifted the way we talk about men’s clothing. He’s a New York City renaissance man, a friend of Drake’s, and great company over a drink or two. 

On a cool, late afternoon on Prince Street, Mezcal on the rocks and the regulars, tourists and cool kids gradually filtering into Fanelli Café — that old-meets-new-meets-scene boozer with the neon sign, the okay food and the impeccable atmosphere — Josh imparts us with some words of wisdom. Lessons on comfort zones, colour, and “dressing for the sidewalk.”

On Colour

Am I colour guy? Yes. I love wearing colour, I only recently started wearing black. I never wore black my whole life. For me, growing up in the 90s, back then it was really about matching your sneakers to your t-shirt, to your hat. So if your stuff was off a bit it could cause trouble for you in the hallways in school. It helped me to develop a keen eye for colour, matching, pairing and working with complementary colours. Lessons that I use to this day.

On Work

I’ve only had three jobs that weren’t in fashion. I was an apprentice sushi chef, I was a line cook and I made bagels. Other than that I’ve only ever worked in this business, so I’ve done it for a long time. There are all sorts of issues with fashion, but at the end of day it’s about human identity, it’s protection from the elements. These are the things that make clothing important. 

You don’t get involved in it unless you love it. It’s not a get rich quick kind of business. I know a lot of people who don’t love what they do. I know a lot of people who do things to support their families, and there’s honour in that. Being able to say I love what I do is a very, very privileged position to be in.  

I happen to be able to support my family doing what I love, and I try and bring that thought process to each day, no matter how frustrating things get. No matter how many flaming bags of… you know what are thrown onto my plate. And so far so good, you know? So far so good.

How’s that for a monologue?

On Stepping Outside of your Comfort Zone

You need to be resilient. I try to take jobs and do things that I’ve never done before. I always want to learn something new. I started out in retail, visual merchandising, then I went to work in magazines for 10 years. I started out at The Fader in 2001. There were eight of us in total at the time, so you gotta learn how to write, because shit needs to be written. You gotta learn how to style, because shit needs to be styled. Edit photographs, because shit doesn’t do itself. You need to learn how to wear many hats. You need to be versatile and flexible.

On New York City Style

New York is a cultural capital city. London, Paris, Tokyo, Hong Kong, Shanghai, there are others of course. These are big cities where a lot of people live, and you live your life in public.

I lived in LA for a while, and everyone stays in their house or their car. The clothes that you wore were important, but more important was what people thought of your house or your car.

Here, your life is on the sidewalk. I’m a sidewalk guy. You need to learn how to dress to convey who you are, what you’re into. Don’t take me for a fool. I’m not easily robbed. All of that is conveyed through what you wear, your demeanour. You learn how to read those cues. To that extent I’ve always tried to dress like myself. The most successfully dressed people in any city are the ones who look like they’re comfortable in their environment, and in their own skin.

On Wearing Your Friends’ Clothes

I want my clothes to be made by people I like. As I’ve gotten older that’s become a really big thing. Good people, definitely. Friends, hopefully. I’m lucky enough to know people who make great clothes. Going back to it, it’s a small community, you’ve got to support each other.

On Modern Menswear

It definitely got flattened out by that Tumblr, instagram wave. It used to be that, if you dressed like a punk, you listened to punk, or were an anarchist and you believed in certain things and you identified with that group of people, and there would inevitably be others who would want to beat you up for looking that way, but now anyone can dress punk. 

There’s been a decoupling from image and meaning. Part of that is social media, but part of it is that people don’t care as much. It’s remix culture. You could dress preppy, but be… in a Norwegian death metal band. Before that you might not equate one with the other. In one way it’s homogenised, in another it’s all over the place. 

On Dressing to Stand Out  

A lot of men in the world don’t want to dress to stand out, they want to dress to fit in. There’s still an idea that taking clothing too seriously is a mark of being unserious as a person. I don’t know if that’s still the true connotation.

I think a lot of tech, or powerful people dress badly because it makes them feel superior to others who take it seriously, like they have more important things to worry about, which is bullshit. There's nothing frivolous about wanting to look and feel good. 

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