Style Strategies
⇾ Jake Woolf, Menswear Writer
On splurging for comfortable shoes and the brands he’s eyeing at the moment

Jake Woolf has spent over a decade immersed in the world of men's fashion, contributing to classic publications like GQ and Robb Report, along with more modern online outlets like Highsnobiety and the now defunct Four Pins. His expertise spans from spotting early trends to breaking down why something looks so damn cool, which is why his social media and Substack are so damn entertaining and enlightening. Whenever I see Jake, he looks put together and always has a new item or brand he wants to talk about. During the time I was interviewing him, he tells me that he's currently working on a newsletter, along with edits for an upcoming TikTok. “The newsletter (which will be out by the time this gets published) is about a pair of pants that I've decided are going to be my go-tos this summer,” he confides. “And once that's done I'm gonna get cracking on a script for a paid partnership video I'm shooting in the next couple of weeks.” I wanted to know more about what he's into at the moment, so I subjected him to the Style Strategies interrogation. He thankfully obliged.

Describe your personal style in five words or less.
Worshipping at the Ralph Lauren altar.
Something you’re looking to buy
at the moment?
A vintage watch, and likely a Cartier Tank. I love my Rolex Datejust that I got brand new a couple of years ago, but think my next timepiece pick-up will be something that was made before I was born.

Magic Carpet bites,
from $4.50 by BonBon
What’s the best thing you’ve bought under $20 recently?
A bag of candy from that spot BonBon that will probably be gone by the time I finish answering these questions. It was like $18—a lot for candy—but they make these little rainbow-colored, sugar-covered, tape-shaped things that are I'm sure nutritionally the worst thing one can eat, but are also absolutely delicious.
What’s been the hardest item to pull the trigger on?
I've wanted a made-to-measure suit for basically my entire adult life, but because of the time and financial commitments they entail, I just never got around to it. But recently I ended up getting one on the house from J.Mueser (I'm working on a video about the process), and, though I was very luckily able to skip the money side of the equation, I can't stress enough how much of a difference it's made in terms of getting a suit that really, actually fits. The whole thing was also just a lot of fun—picking out fabrics, going in for fittings, etc.—and ultimately, it's made every other suit I own feel uncomfortable by comparison.
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Three favorite brands, currently?
Taiga Takahashi, A.Presse and 18 East.
What’s your footwear rotation
look like lately?
I honestly don't know why—maybe I'm just getting older—but recently I've been leaning heavily into grandpa-approved, foot-friendly shoes. That means I'm currently sitting on a rotation that consists of four pairs of Mephistos—one of their iconic “Match” silhouette, two from their 18East collab, and one pair of the Rainbows. I've also got a pair of orthopedic shoes from a Danish brand called Jacoform that, while I wouldn't call “good looking” in the traditional sense, are genuinely the most comfortable shoes I've ever owned. That said, when I do want something a little more classically handsome, I've been reaching for this pair of moc toe loafers from Banana Republic that are made from a super-soft leather, which makes them great for all day wear and going sockless in summer.

Match sneaker,
$399 by Mephisto
Do you shop more online
or in person?
Despite the fact that I do so much online product recommendation content, I still prefer to buy things in person. You just never quite know how something is going to look and fit until you can experience it in real life, and being in New York, I pretty much have access to every product I'd ever want, so I'm super grateful for that.
Best city for shopping?
It's probably Tokyo, but I've actually never been there. (I'm working on it for later this year.) So for that reason alone I'll say New York City has the best shopping—there's literally just something for everyone and every kind of style, whether you're looking for a bespoke suit, a rare pair of sneakers, incredibly curated vintage, and everything in between.
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Necessary extravagance?
A good haircut. It's something you've gotta live with 24/7, you know? So I'm willing to pay top dollar for a cut if I know the results are going to be great.

Everyday socks,
$22 (for three pairs) by Nike
The one thing you’re cheap about or refuse to spend money on ...
I'm not against nice socks, but I don't splurge on them because I tend to lose them so often, whether mysteriously in my apartment or when traveling. So 99% of the time I'm just wearing black Nike Dri-Fits.
What’s something you buy multiples of (either by design or by default)?
I'm a big fan of Abercrombie's premium heavyweight cropped tees—they're my go-to in summer, so I own like six of them. Also, Skims boxer briefs are genuinely excellent, so I recently just got another six-pack of those to go with the four pairs I already own.