No One Knows the Rules of Style Better Than Jian DeLeon

Flip-flops?

Only if I’m by the beach.

Black and navy?

Always a yes.

Black and brown?

Also a yes.

Tan dress shoes?

Always a no.

What’s one trend you don’t like?

The fact that everything has to be a trend. With TikTok and the algorithm, there’s a new “core” every other day, and I advocate people being able to explore their personal sense of style, not chase a new aesthetic every day.

So how do you feel about trends, generally?

In menswear, trends are all about nuance. Certain patterns and colors ebb and flow in popularity. But the whole notion behind trends is giving people a reason to look at what’s coming to stores and what are the pieces in their wardrobe that they need a new version of.

What do you revere in style?

I work in Columbus Circle in New York, and once or twice a week I go down to Times Square. It gives a good cross section for how the average customer is dressing today, what makes them feel good and look good. It’s super important to have that awareness of how the average person wants to put an outfit together.

What never goes out of style?

Developing really great taste and making choices informed by that personal taste level.

Suit, shirt, and tie by Thom Browne. Shoes by John Lobb. Socks by Pantherella. Glasses by Tom Ford.

How much is too much to pay for a pair of socks?

It’s relative. A lot of people don’t know that socks were a symbol of the aristocracy, a luxury. Something to cover your feet before you put on shoes is a form of decadence. Some people, their feet run cold, so it makes sense to invest in a pair of cashmere socks. I’m a fan of sticking by the tried-and-true things you know and love. I have so many pairs of Nike Dri-Fit socks that I’ll wear with anything.

What was your aha moment when evolving your personal style?

A lot of my personal style came from subcultures. I was into music before I was into clothes, so I grew up listening to a lot of punk and hardcore from the Washington, D.C., area. There’s a store called Smash where you could get tees with the Fugazi logo on it. They also had a lot of Vans and some old Levi’s, too. But it was also this formative time in D.C. where you had stores like Commonwealth and Major, where the sneaker scene was booming. I was working at the Urban Outfitters in Georgetown and spending a lot of my money at these other stores. So it’s always been informed by things I was into and the uniforms that these tribes wore, but mixing them together in my own way.

What’s your one go-to style rule?

Pants are the most important thing in an outfit. They have to fit perfectly. To quote The Big Lebowski, they’re the rug that ties the room together.

Photography: James Macari
Sittings Editor: Alfonso Fernandez Navas
Hair: Kevin Ryan using Unite
Grooming: Ryo Kuramoto for Nars
Design Director: Rockwell Harwood
Contributing Visual Director: James Morris
Executive Producer/Director: Dorenna Newton
Director of Photography: Elyssa Aquino
Camera: Derrick Saint-Pierre
Video Editor: Josh Archer
Associate Producer, Video: Janie Booth
Associate Producer, Video: Carly Bivona