Jake Woolf

Articles

Here’s Exclusive Access To Over 50 Great Vintage Items

4 days 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.
These Shoes Are More Comfortable Than Mephistos

1 week ago | jakewoolf.substack.com | Jake Woolf

Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes. Read Shoesday 1, 2, and 3 here, here, and here. Before we get to the main subject of today’s post, know that the winner of my size 9.5 Banana Republic Moc Toe Loafers, which I wrote about here, will be emailed today, May 6.
The Best Pants For Summer Aren’t What You Think

1 week ago | jakewoolf.substack.com | Jake Woolf

Today’s post is in “Recommendation Compilation” form, which means below you’ll find a round-up of my favorite style stuff from the week that was, including: The pants I’ve been wear testing all week, and which have catapulted to the top of my summer trouser rotation for one important reason.
16 Stylish Guys On Their Favorite Summer Shoes

2 weeks ago | jakewoolf.substack.com | Jake Woolf

Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes. Now that some warm weather has finally, mercifully arrived on the East Coast, I thought it was the perfect time to compile a list of shoes that are specifically tailored to summer enjoyment—the kinds of footwear you’ll rock alongside your breeziest shirts, flow-iest shorts, linen-iest suits, and more.
The $800 Spring Jacket That’s Sold Out Everywhere

2 weeks ago | jakewoolf.substack.com | Jake Woolf

Hey, it me, reporting live from light jacket season—that glorious, short-lived weather sweet spot that comes but twice a year here on the East Coast. Stylistically what this means is that from now until roughly a month from now, each day presents a golden opportunity to put one’s best windbreakers, trucker jackets, Harringtons, and more on full display as the centerpiece of a spring fit.
Shoesday #2: A $200 Loafer That Looks Like A $1,300 Loafer

3 weeks ago | jakewoolf.substack.com | Jake Woolf

Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes. Over the weekend, my friend Lawrence and I were talking about clothes, as we often do.
My 50 Favorite Button Up Shirts For Spring-Summer 2025

3 weeks ago | jakewoolf.substack.com | Jake Woolf

While button-up shirts can often be relegated to under layer duty in the dead of winter, hidden beneath sweaters, coats, and scarves, when things heat up they enter center stage in one’s wardrobe. Now, on the one hand, that places added importance on finding the right button-up shirt to set your fits on the right track. But on the other, when you do dial in a great one, you can take solace in knowing any look is effectively already half way there.
Shoesday #1: My 20 Favorite Loafers To Buy Right Now

4 weeks ago | jakewoolf.substack.com | Jake Woolf

This is the first edition of a weekly, footwear-centric column I’m calling “Shoesday.”Whether I’ve been penning a trend piece on the rise of the Paraboot Michael, creating a column dedicated to the latest hyped up sneaker, or generally just being a sicko who continues to cop despite owning more footwear than I could possibly wear in a lifetime, shoes are without a doubt the clothing category I’ve thought the most about throughout my style career.
L.L. Bean Japan Is Finally Available in America (Video)

1 month ago | jakewoolf.substack.com | Jake Woolf

For the first time since launching in 1992, LL Bean Japan can now be purchased by American shoppers for a limited time only. (More specifically, this weekend only). So I stopped by the Brooklyn pop-up, located at 96 N 5th Street, to check out the offering.
How To Get 15% Off Bare Knuckles’ New Releases

1 month ago | jakewoolf.substack.com | Jake Woolf

If you’ve been following me (and this Substack) for any time at all, then you know how big of a fan I am of the small Portland-based label Bare Knuckles. In my opinion, the label consistently puts out some of the highest quality, best-fitting, coolest-looking classic gear on the market—whether we’re talking about their perfectly-washed made-in-USA wide-leg jeans, tastefully distressed work jackets, or beefy homegrown hoodies and sweats that I genuinely seldom take off.