Christopher Fenimore

IN THIS column, I feature people with some of the best personal style in the world, and everyone is in play — homies included. This week, I bring you Jeff Hilliard, my first #menswear buddy. We met through Tumblr, but quickly became real friends. I always loved Jeff’s blog and admired his style, but I also appreciated that he was more down-to-earth than most bloggers who were into tailoring. He never took it too seriously, and yet he also approached it sincerely. We’ve aged together through various career and life twists, and while I can safely say I experimented with some styles and brands that weren’t me, Jeff’s stayed consistent through it all — everything he owns fits him impeccably.

Below, Jeff and I discuss how comfort plays into personal style, tips on sourcing and purchasing vintage watches, and plenty more.


Fit One

Christopher Fenimore

“The people with the best personal style are comfortable, and look comfortable, right?” he says. “That can be people in dad-wear all the way through to avant-garde stuff, but they wear it in a certain way that looks fresh and super cool. I’ve seen guys in jeans and a T-shirt look more put together than guys in full suits”

Let’s orient you for readers. What do you do for a living, and what were you doing prior to your most recent gig?

I’m currently the director of limited editions at Hodinkee, so that means my team and I work together to work with brands and make fun products, everything from watches to accessories. We’re going to start branching out of that as well in the next few years; you might see some furniture pieces. It’s a pretty creative job. Before that I had a stint at Mr Porter. I managed the personal shopping team there for three years. Prior to that, my foray into luxury was The Armoury. I started in the shop and then moved into the digital commerce side, and was there for four and a half years.

What does personal style mean to you and how have you refined yours over the years?

The people with the best personal style are comfortable, and look comfortable, right? That can be people in dad-wear all the way through to avant-garde stuff, but they wear it in a certain way that looks fresh and super cool. I’ve seen guys in jeans and a T-shirt look more put together than guys in full suits. It’s rarely about a single piece of clothing, it’s more about how they’re wearing it. When I’m thinking about dressing, the main thing I’m thinking about is not necessarily the pieces that I’m wearing—although that’s important when I’m buying stuff—it’s more about how I would put them together. What makes sense where it actually feels like it’s part of me. My number one thing is if I’m not comfortable in something, I’m going to look like a moron.

Fit Two

Parka by RRL, puffer by Patagonia, chinos by The Armoury, shoes by Alden, Christopher Fenimore

Watches can be a feeling-based thing,” he says. “I don’t have many watches but I might wear one because that’s what I feel like wearing that day. If I know I want to be casual I might throw my Rolex Submariner on, and that’s going to tell me, all right, I’m not wearing a suit that day. I’m not going to rock a Sub with a suit.

Christopher Fenimore

Now, I’ll build an outfit around a watch that I want to wear, but not all the time,” he continues. “In the past, it was never that.

Christopher Fenimore

Why and how do watches and menswear synthesize?

JH: I wouldn’t have thought about this until I really started to work in watches, but I realise now that I was thinking about it even unconsciously. The easiest way that I think about it is it’s just another thing to play around with. Watches can be a feeling-based thing. I don’t have many watches but I might wear one because that’s what I feel like wearing that day. If I know I want to be casual I might throw my [Rolex] Sub[mariner] on, and that’s going to tell me, all right, I’m not wearing a suit that day. I’m not going to rock a Sub with a suit. So, that’ll actually play into how I dress that day. Now, I’ll build an outfit around a watch that I want to wear, but not all the time. In the past, it was never that.

Are you on the hunt for any watches or clothing items? Which and why?

Always. I’m on the hunt for a very specific Cartier. I got close two years ago. Someone was ready to sell it to me and they decided not to. It was a family heirloom, so I totally understood. But it’s a specific type of Tank Allongée that was a pretty early model Tank. It was one of the first three or four models that they had created. It’s a non-curved Cintrée, basically. This one specifically has what they call “eagle beak” lugs, so it’s very flat and then it curves at the end. As for clothing, I’ve been wanting to wear suits more lately, but not in the way that I used to wear them, so more casual. I’m not really wearing ties very much unless the situation calls for it. My whole thing now is I want some suits that I can wear belts and silly, dumb shoes with—ones that don’t go with suits—and anything up top besides a dress shirt, but still look really slick. I’ve got a couple suits on order from a tailor I like that’ll probably arrive in the next year or two.


Fit Three

Suit by Panico, denim shirt by Levi’s, shoes by Crockett & Jones, sunglasses by Celine glasses, watch by Timex by Hodinkee, Christopher Fenimore

I’ve been wanting to wear suits more lately, but not in the way that I used to wear them, so more casual,” Hilliard says. “I’m not really wearing ties very much unless the situation calls for it.

Christopher Fenimore

I actually have started to go to women’s clothing stores a bit because I think what they do is more interesting than the men’s side a lot of times,” he says. “I’ll pick accessories out here and there from women’s: belts, sunglasses, you’ll see in the photos. I’m more open to that now. I’m confident enough that it doesn’t really phase me.

Christopher Fenimore
Christopher Fenimore

What are some of your favorite retail stores, and why are they favorites?

C’H’C’M’ has been doing high level stuff for 10 years, but I think in the past three or four years, especially as things have changed with COVID, their game is really high. I’m always in and out of The Armoury. Obviously, I used to work there, and the reason why I worked there is because I love the clothes, and I still do. I’m obviously a huge fan of Stoffa and shop a lot there. What Nick and Agyesh do is big. I think the new Drake’s store on Canal is a can’t-miss. For basics, Andrew at 3sixteen always has me covered. I shop at Acne quite a bit for denim, and there’s always some good stuff to see there. I actually have started to go to women’s clothing stores a bit because I think what they do is more interesting than the men’s side a lot of times. I’ll pick accessories out here and there from women’s: belts, sunglasses, you’ll see in the photos. I’m more open to that now. I’m confident enough that it doesn’t really phase me.


Fit Four

Coat by Stoffa, hoodie by The Real McCoy’s, trousers by Ambrosi, shoes by Paraboot, scarf by Drake’s, watch by Rolex, Christopher Fenimore

When it comes to buying a vintage watch, “first, do your research,” Hilliard says. “If you really like it, it will be easy to do the research because it will come naturally and it’ll make you more excited.

Christopher Fenimore

There are a number of different vintage dealers that you can trust to find you the top tier of the market,” he continues. “If you have the money, I would suggest going to them because they’re going to do a lot of the work to find it for you.”

Christopher Fenimore
Christopher Fenimore

What advice do you have for someone looking to buy their first vintage watch?

Some of my colleagues could probably answer this question better than me, but I would say two things. First, do your research. If you really like it, it will be easy to do the research because it will come naturally and it’ll make you more excited. The other thing I say specifically about watch buying is it’s really easy to get excited about a watch and think, “Oh, I need this.” I always tell people, think about it for a month. If after a month you’re still excited, that’s good news. Sit on it for another month, and after two or three months, if you’re still excited, that’s the watch you should buy. With watches, I think it behooves you to take the time.

Outside of that, in terms of actually finding the watch it’s kind of a small game. There are a number of different vintage dealers that you can trust to find you the top tier of the market. If you have the money, I would suggest going to them because they’re going to do a lot of the work to find it for you. You just have to pay the money, but sometimes it’s worth it. If you don’t have the cash for that, then I think that’s where the research comes into play. Either you’re comfortable with something like eBay, or you go to a trusted source, a place like Hodinkee, or Crown and Caliber, that has a lot of stock, or smaller outfits, like Chrono24, where there’s private dealer-to-dealer stuff.


Fit Five

Chore coat and shirt by Drake’s, jeans by Acne, belt by Rubato, sneakers by Tarvas, Christopher Fenimore

Certain pieces of clothing or accessories or objects, whatever they may be, can have really significant personal value,” Hilliard says. That’s one area I don’t think it can be minimised: how important some of those things can be to ground us.

Christopher Fenimore

There are a lot of small makers that you can support. I’m lucky enough that some of them are my friends,” he continues. “It’s amazing when you can support a small brand that happens to be your friends, and you’re also absolutely jazzed about the stuff that they make.

Christopher Fenimore
Christopher Fenimore

You wrote a heartbreakingly beautiful piece in 2021 for Hodinkee about your dad, his Rolex, and your journey to reclaim it after it was stolen from you. You touched on this in the piece, but how can consumerism and luxury play a positive role in this world?

Listen, you have to admit, especially now, there’s rampant consumerism. I’m a part of this. It’s just a fact. And that is not a good part of the industry. It’s something I don’t think anybody’s really proud of. Obviously a lot of it is profit-motivated. Innate profitability and taking the consumer for a ride is part of the industry, and there’s not much we can do about that. The positive part of it, and the part that really brings me into it, is twofold. One is that certain pieces of clothing or accessories or objects, whatever they may be, can have really significant personal value. This watch, for instance, for me. It’s just a watch and it’s truly not anything special. It’s a Rolex just like any other. There are millions. Obviously, it’s one of my most prized possessions because it reminds me of my dad, and now it reminds me of everything I went through to get it back. So that’s one area I don’t think it can be minimised: how important some of those things can be to ground us.

The second thing is, for me, the most interesting part of clothing now: There are a lot of small makers that you can support. I’m lucky enough that some of them are my friends. And so, I buy Stoffa, not just because Nick and Agyesh are my friends, but because it’s genuinely good clothing. It’s amazing when you can support a small brand that happens to be your friends, and you’re also absolutely jazzed about the stuff that they make. Same thing with tailoring. Yes, bespoke tailoring is incredibly expensive and stuffy, and some people think it’s ridiculous. That’s true. But I might buy one thing a year, and that’s going to last me for 15 years. I love the fact that I’m giving that money to somebody that is actually doing it. Derek Guy writes a lot about this type of stuff, and he’s obviously been a hot topic of conversation lately. But I think one of his through lines is he misses the days when that used to be more available. I really think participating now in consumerism is more fun because I can support people that I like.

If you had to wear one outfit for the rest of your life, what would it be?

I’d have a dark brown pair of loafers. I’m going to leave accessories out. Mid-wash, super-heavy denim. My overcoat from the first outfit. A super nice overcoat that basically can be worn with anything from jeans all the way up to a tuxedo. Then a cashmere sweater with a really heavy cotton T-shirt underneath. So it’s like all seasons, all situations.

This article was originally published on Esquire US.

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