Archive - Jake Woolf

August 2025

Everything I Packed For My Trip To Italy, Round 3

This time, everything is going in a carry-on. Wish me luck.

Aug 31 •

My Top 10 Footwear Market Predictions

Part 1 of my thoughts on where to invest your time and money in terms of various shoe trends.

Aug 26 •

The 101 Best On-Sale Style Items To Buy Right Now

All of the discounted menswear that you won’t regret buying.

Aug 24 •

Here’s Exclusive Access To 50 Awesome Vintage Items

I teamed up with one of America’s premier vintage stores, Wooden Sleepers, for early access to their latest drop.

Aug 21 •

Jake Woolf x Wooden Sleepers Vintage Drop Preview

Wooden Sleepers’ Brian Davis and I go through some of the highlight’s from tomorrow’s exclusive early access release.

Aug 20 •

25:50

Here’s 25% Off My Favorite White Sneakers

Why the Mephisto Rainbow has not only become an icon, but my personal go-to.

Aug 19 •

Here’s A Subscriber-Exclusive Version Of My Favorite Nylon Shorts

I teamed up with Manresa on a limited-edition run of their Made in USA Ravine shorts.

Aug 16 •

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