Style Strategies

⇾ How Christopher Fenimore Shops

Style Strategies

⇾ Christopher Fenimore,
Photographer

The stylish lensman on the benefits of tasteful networking and why you should buy with intention

Photographer Christopher Fenimore

Our three previous ‘Style Strategies’ features have one unique thing in common—they've all been photographed by Christopher Fenimore. Responsible for some of the most memorable (and re-grammed) street style images on the web, he also shoots for the best menswear labels and shops, from Eighteen East and Stoffa to The Armoury—to namecheck just a few on his ever-expanding client list. Chris has a keen eye for details whenever he shoots someone's outfit and even has a column that I check out weekly from Esquire devoted to personal style. Chris jokingly admitted that he never gets to do this sort of thing, since he's usually on the other side of the camera, inquiring about his subjects' interests.

Chris' personal style is more of a uniform, he says, but he knows how to throw in some standout pieces that your average fashion enthusiast might not be able to pull off. And that's no accident, given his background. Before becoming a freelance photographer, he was working at a fashion favorite New York shop called Carson Street Clothiers during the height of the #menswear era. Currently one of the top street style photographers in the game, his insider access and easygoing personality allows Chris to capture some of the best-dressed guys in fashion today. We caught up with him between shoots to see where he's been shopping, what brands he's currently watching and if there's anything he refuses to spend money on.

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Photographer Christopher Fenimore
Photographer Christopher Fenimore

Describe your style
in five words or less.

Umit Benan meets Haider Ackermann.

Canon EOS R5 Camera

EOS R5 camera,
$3,899 by Canon

What are you shopping for at the moment?

Right now, just another RF lens for my R5.

Canon EOS R5 Camera

EOS R5 camera,
$3,899 by Canon

How did the ‘Five Fits With’ series come about with Esquire?

I started it in a slightly different format, with no text, on my Tumblr over a decade ago and called it ‘In Medias Res’. I continued the series for Four Pins and later added an interview component with Grailed. When Grailed no longer wanted to continue the series with me, I posted on my Instagram story that I was looking for a publication to pick it up. Luckily Jonathan Evans at Esquire was interested.

For people that may not know, you worked for Carson Street Clothiers back in the day. How did that help with your current freelance position today?

I was there from the beginning to the end. I started as a sales associate working the shop floor, but both owners, Matt and Brian, promised me a “job-job” when I graduated college and when I did, they offered me the role of Associate E-Commerce Director. I was responsible for photographing products, content, styling, product copy, sales and whatever else we needed for the site. We all wore a lot of hats to keep that shop running. I met a ton of people, whether they were customers, buyers, designers or other photographers and stylists. It was a hub for menswear in the city, and we had visitors from all over, but I was also lucky enough to come along on the buying trips and meet others internationally. I built an incredible network and learned how to continue networking tastefully. I also learned the scientific side of photography in taking product shots and the artistic side in shooting street style and constant content.

Any advice for someone trying to make it in fashion photography?

I really don't think I've made it in fashion photography. It took me a while to figure out that it was not going to happen for me and be okay with it. I feel I capture people well, and I'm obsessed with clothes and fashion, so I think I'll always be in that world in some capacity. Honestly, I don't have advice regarding “making it” because the market is saturated with people clamoring to get in. I'd say try your hand at street style because the variable of quickly changing light, environments and subjects will teach you how to use your camera in a way not much else can. Also, be kind to every single person you meet.

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Any brands you’re watching right now?

Drake's, Lemaire and Massimo Alba.

Mr. P Navy Unstructured Worsted Wool Blazer

Navy unstructured
worsted wool blazer,
$480 by Mr. P

What’s one garment that every man needs in his closet?

I think it's got to be something classic yet slightly casual. A navy unstructured blazer.

Mr. P Navy Unstructured Worsted Wool Blazer

Navy unstructured
worsted wool blazer,
$480 by Mr. P

The Elder Statesman Italy Smoking Jacket

Italy smoking jacket,
$2,195 by The Elder Statesman

Do you have an piece you’ll never part with?

An insanely soft Elder Statesman cashmere smoking jacket.

The Elder Statesman Italy Smoking Jacket

Italy smoking jacket,
$2,195 by The Elder Statesman

How do you like to shop?

I've been shopping online more and more, since New York shopping is pretty dead, lately. Though I think C'H'C'M' is one of the best stores anywhere, and definitely the best men's store in New York.

Do you ever buy things in multiples?

T-shirts. Every body type is different so when you find one that fits you, you should grab a few. You never know when they'll be discontinued.

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What city has the best shopping?

I haven't been to an insane amount of cities, but Tokyo blew me away. Unfortunately, I was only there for five days, but there is something for everyone. The average person cares so much about their appearance, but in an unimaginably tasteful way that I've not seen anywhere else. I don't buy anything specific, but I look for brands or items native to the place I'm traveling to as there will be no doubt exclusives and better prices.

Necessary extravagance?

Organic groceries and wines, and grass-fed, pasture raised proteins.

What is something you refuse to spend a lot for?

Honestly? Probably clothing.

Which do you experience more: buyer’s remorse or regret for not buying something?

Oh, definitely regret for not buying something. It's the worst when you miss the last item or lose an opportunity to pick up a rare one. It took me a long time to realize buyer's remorse means you're buying too much and not thinking enough about your purchases. That's a big lesson.

What’s one shopping hack that you can let everyone know about?

Buy less and wear your stuff more. If every year you're sick of what's in your closet, you're not buying the right things, and you haven't figured out what your style is yet. It takes time, but don't spend half of your paychecks trying to figure it out.

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