Jake Woolf

1 week 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.

1 week 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.

1 week 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.

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

On a trip last month to elite-tier menswear outpost (and certified danger to my wallet) CHCM, I came across a rather unique version of a classic Type III trucker jacket. Instead of the typical denim, this one was done up in what I can best describe as a brushed, featherweight chino. I tried it on, and instantly fell in love with the cropped fit and airy feel of it. It was mere moments later, however, that I clocked a pair of painter pants, hammer loop and all, rendered in the exact same fabric.

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

In today’s post you’ll find the following: My new, old man-approved sneakers The current leader in the clubhouse for “Pants Of The Year 2025” The (now sold out) jacket I’m kicking myself for not buying My 6 favorite heavyweight tees for people like me who prefer a lift heft in their summer short sleeve knits… And last but never least, a non-heavyweight tee that I’ve been wearing as my go-to undershirt for weeks Let’s get to it…enjoy!!! And now, for today’s post… Keep reading with a 7-day free...