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1 week ago | 
jakewoolf.substack.com | Jake Woolf
Welcome to Shoesday, a weekly column, sent every Tuesday*, about shoes. *This post is being sent out on a Wednesday because I was traveling. To see everything I packed for my trip, click here. I don’t remember exactly when I first came across Morjas—though, chances are it was on Instagram, where the algorithm correctly marked me as the kind of person who will stop scrolling for a pair of Goodyear-welted loafers captured in perfect afternoon light.
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1 week ago | 
jakewoolf.substack.com | Jake Woolf
Tonight I’m flying to Italy for a week—Florence is up first, then Milan. The main reason for the trip is work: more specifically, I’ll be making videos for Pitti Uomo’s official instagram account all week before heading to Milan for a couple presentations that a few of my favorite brands (namely, Ralph Lauren and Brunello Cucinelli) are putting on.
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2 weeks ago | 
jakewoolf.substack.com | Jake Woolf
Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes. Hope you’ve gotten that pedicure, because toes-out, sandal season is officially here. Now, the question of where you should wear your sandals is one that’s still hotly debated in menswear circles, but I’ll get my take out of the way now: I tend to fall on the “do whatever you want” side. To me, if you’re bold enough to wear rubber flip-flops on the uptown train, I won’t stop you.
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2 weeks ago | 
jakewoolf.substack.com | Jake Woolf
Over the last few weeks I worked on an Instagram project with Shopbop, where, during the planning phase of the gig, I was able to select products from the hundreds on their website to highlight in a series about summer style. As I poured through pages upon pages of gear, I stumbled upon a T-shirt that, at least through my phone screen showed promise—the fit and wash look pretty nice, I thought—but which came from a brand I had never heard of before called Asher.
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3 weeks ago | 
jakewoolf.substack.com | Jake Woolf
Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes.
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4 weeks 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 month 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 month 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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1 month 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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1 month 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?