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3 days ago | 
jakewoolf.substack.com | Jake Woolf
Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes.
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1 week ago | 
jakewoolf.substack.com | Jake Woolf
This weekend, meaning today, Friday May 30 and tomorrow, May 31, I will be doing a massive purge of my closet and selling a bunch of stuff at Alfargo’s Marketplace live from New York City. (The specific address is 110 East 25th Street.) There will be all sorts of goodies, from jackets to shirts to pants, jeans, shoes, and some other stuff I might grab between now and when the event kicks off at 6PM.
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1 week ago | 
jakewoolf.substack.com | Jake Woolf
Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes. It wasn’t that long ago that dad shoes were a punchline. One that referred to the kind of footwear that prioritized comfort over aesthetics, came in exactly one color (grass-stained white-ish), and looked like they were designed by someone who has more interest in preventing bunions than big fits.
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1 week ago | 
jakewoolf.substack.com | Jake Woolf
Despite the fact that it was oddly cold and rainy in New York this week, I haven’t forgotten that summer—in all of its sunny, relaxing, leaving work early on Fridays glory—is, as we enter Memorial Day Weekend, imminent. Before you know it, your waxed jackets, 18oz denim, and hefty derbies will all take their seasonal sabbatical to the back of the closet, replaced by the breeziest, sweat-deflecting, SPF-compatible gear you can get your hands on.
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2 weeks ago | 
jakewoolf.substack.com | Jake Woolf
Canoe Club: one of the most quietly consistent, elite-tier, and personally speaking, favorite menswear shops in the entire country. If you’re unfamiliar, they’re based in Boulder, Colorado—but don’t let the non-coastal coordinates fool you. Since 2017, they’ve been curating a brand lineup that can hold its own against just about any retailer on the planet.
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2 weeks ago | 
jakewoolf.substack.com | Jake Woolf
Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes. I recently did a round-up of my favorite loafers on the market, which, if you’re interested, you can check out here. But for those sticking around, today I’m circling back to the subject of these stylish, timeless slip-ons, but through a slightly different lens. Instead of scouring the market for new options, this entire 50 item (!!!) list is dedicated exclusively to pre-owned loafer gems. The main reason for doing this?
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2 weeks ago | 
jakewoolf.substack.com | Jake Woolf
I first came across the burgeoning LA-based label Cobra SC a few years ago, when its sultry button-up shirts and tailored suits began making waves among the city’s artist and indie rocker cool guy set. But I didn’t have any IRL experience with the brand until this past February, when founder and designer Safa Taghizadeh invited me to a low-key preview of the latest offering at the Bowery Hotel. In short, I left the room thoroughly impressed with the range.
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3 weeks ago | 
jakewoolf.substack.com | Jake Woolf
The second floor of an office building in New York City’s Garment District might not be the first place you’d expect to find one of the world’s best menswear shops, but that’s precisely the case with No Man Walks Alone.
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3 weeks ago | 
jakewoolf.substack.com | Jake Woolf
Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes. In summer the vibes are supposed to be relaxed, and for me, that means I want my shoes to get the memo, too. Rather than hefty and chunky, when it comes to lacing up some footwear between June and August, the main things on my mind are breezy, sleek, and light—save for the occasional pair of sturdy penny loafers when the occasion calls.
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3 weeks ago | 
jakewoolf.substack.com | Jake Woolf
Good Form in Chicago is, to put it plainly, one of the best vintage retailers in America. Founder Cale Darrell, who launched the business in 2019, has an eye for curating the best of the best in terms of throwback workwear, Americana, and prep that’s second to none—and which stems from a desire to present vintage in a fresh, elevated way. “My main goal was to get out of the ‘Cracker Barrel’ vintage vibe,” he says.