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Style Strategies: Jake Woolf, Menswear Writer

May 8, 2025 by 0 Comments

Style Strategies: Jake Woolf, Menswear Writer
Fashion

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.

Mephisto Match sneaker

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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