Christopher Fenimore Photographs the World's Most Stylish Men. Here's What He's Learned.

Christopher Fenimore@jamesmacari

You can usually find Christopher Fenimore on the other side of the Esquire camera lens. Turns out, photographing and interviewing scores of the most influential figures in the industry makes you pretty damn influential yourself. For “Five Fits With,” his weekly style column on, Fenimore has shot and interviewed Sir Paul Smith, Wyclef Jean, and Apple Music’s Zane Lowe, to name a few. He also handpicks lesser-known menswear enthusiasts for his column: the stylists, vintage experts, and small-shop owners from across the country who can really nerd out about the details with him. Regardless of whom he’s photographing, the Brooklyn-born Fenimore—who now calls Long Island home—shows up to every shoot like he could be the subject of his own column. So we decided to ask him about his own views on style, trends—and whether boat shoes are actually back.

Esquire: What was your aha moment involving your own personal style or your approach to dressing?

Christopher Fenimore: I used to check all the fashion shows when I was younger. When I stopped caring so much about what people were telling me and instead focused on what felt right to me, that was eye-opening. I think it’s about paying attention to people around you every day.

What’s the difference between style and fashion?

Fashion is an industry. Fashion is very of the moment. Style is something that’s innate; it’s how you translate fashion.

Denim jacket by Umit Benan. Shirt by Visvim. Tank by Comme des Garçons. Trousers by Uniqlo x JW Anderson. Sunglasses by Oliver Peoples. Watch by Omega. Necklaces from Beacon Design.@jamesmacari

A designer you love right now?

I am wearing a couple pieces by Visvim right now. They’ve been doing the same thing for a long time, and I really like it.

Who’s your style icon?

Yasuto Kamoshita, who is a designer out of Japan. He does tailoring but also amazing sportswear. He is personally well-dressed, and his brand, Camoshita, is great. Japan, in general, is also a massive influence—just Japanese style.

Is there a correct length for shorts, and if so, what is it?

There’s definitely an incorrect length for shorts. They shouldn’t be too long. Once they are encroaching on the knee or further than that, yeah, it’s a no for me.

Do trends matter for you personally—and for the world generally?

Trends can matter because they create reverberations and help inform what people are doing, how people are dressing. But for me they don’t really matter anymore. I try hard to just stick with the things that I’ve been wearing for a long time. If I’m buying anything new, I’m trying to make sure it’s timeless and I’m not going to regret it in five years.

What’s your favorite social-media follow in the menswear space?

L’Etiquette, a French magazine doing really great stuff. Also their fashion director, Gauthier Borsarello, he has an amazing Instagram. He’s probably my favorite follow as a person.

a man wearing sunglasses

What’s something that you never wear but absolutely refuse to get rid of?

I have this Prada shirt from the collaboration they did with Christophe Chemin. He’s an artist, and it’s this crazy dress shirt with these big panels with dinosaurs and all this crazy stuff on it. It’s super rare. It’s worth a lot of money, but even though I don’t wear it very often, I’m never going to get rid of it.

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

I’ve started wearing Pantherella, which are moderately expensive. Over $40 or $50 is a little crazy.

One trend you swore you’d never embrace but now you have?

I don’t have baggy pants, necessarily, but I’ve gone a bit looser.

What is an underrated brand that you love right now?

Massimo Alba out of Italy. He does incredible knitwear. Some of my favorite things I own in my closet are from him. Also Stòffa here in New York. It’s pricey, but given what it is, I think they’re undercharging. You get an incredible product.

What’s one thing you buy over and over again?

Uniqlo underwear and James Perse T-shirts.

What’s your go-to cologne?

A bunch of different ones from Le Labo. This is going to sound terrible, but I was wearing it before a lot of you were. I really was. I’m wearing Tonka, Baie, and Matcha right now.

Your ultimate watch?

I think I got it already: an Omega Seamaster De Ville from somewhere in the ’60s. When I had my first good year of freelancing, I bought it for myself as a Christmas bonus.

Are boat shoes actually back?

They’re everywhere right now. Not for me, but they are.

Go-to summer shoe?

Feit slip-on loafers. Those are so comfortable. I wear them to the beach all the time.

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

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