JAKE WOOLF

Share this post

User's avatar
JAKE WOOLF
New York’s Coolest LES Shop Made The Perfect Summer Shoe

New York’s Coolest LES Shop Made The Perfect Summer Shoe

Plus an exclusive, subscriber-only offer on the new Sperry x Colbo collaboration.

JAKE WOOLF's avatar
JAKE WOOLF
Jul 08, 2025
∙ Paid
24

Share this post

User's avatar
JAKE WOOLF
New York’s Coolest LES Shop Made The Perfect Summer Shoe
11
Share

Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes.

For 10% off the Sperry x Colbo collaboration (and your entire Colbo order), use the code below.

Unless you’ve spent the last few years slumbering in some inland cave, then you probably know that a boat shoe wave has recently flooded the footwear market. Today, if you’re feeling ready to hop aboard, then there’s no shortage of options—everything from tried-and-true classics to four-figure ultra-luxury riffs are a simple click away. And yet, one of New York’s City’s coolest shops, Colbo, just injected the nearly 100 year old style with new life by making what might be the chillest pair of boat shoes money can buy.

Boat shoes are already casual-leaning by nature, but longtime wearers know that new pairs can require what might be a months-long break-in period before they truly feel like yours. In an effort to skip right to the good part, designer and Colbo co-founder Tal Silberstein teamed up with Sperry—makers of the OG boat shoes—on a version of their iconic Authentic Original that’s done up in an ultra-soft Italian leather such as to look (and feel) like you’ve owned them for years. “From that first meeting, in my mind it was, like, how do I make it loose?,” says Silberstein. “[I wanted it to be] easy to wear, and able to go anywhere. You can wear it to a summer wedding, when you’re just going to the deli, or the beach.”

Image c/o Colbo

To achieve this pre-worn look right out of the box, Silberstein and Sperry experimented for months, tweaking everything from the soles to the type of leather used—even when in the process the washing and distressing took place. In the end, they landed on a leather sole that was resurrected from Sperry’s 1980s archives and was a more natural fit for the super soft uppers. The colors used—official names: “Distressed Taupe” and “Weathered Sahara”—were also chosen to seamlessly integrate into Colbo’s signature dusty palette, though they’re versatile enough to work in any wardrobe. (I particularly love the way the Sahara color pairs with blue jeans.)

Subscribe to continue reading and get a 10% off code…

This newsletter is ENTIRELY funded by subscriptions. I don’t use affiliate links, and all of these products are things I’ve endorsed because I actually like them—though in some cases I did not pay for them. Point is, your subscriptions are both extremely cool and very much appreciated. Thank you!

Keep reading with a 7-day free trial

Subscribe to JAKE WOOLF to keep reading this post and get 7 days of free access to the full post archives.

Already a paid subscriber? Sign in
© 2025 Omnipotent Inc.
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share