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Fall Guide to Footwear

A guide to shopping some of our favorite fall-ready shoes right now.

Leon Hedgepeth and Sprezza
Sep 02, 2026
∙ Paid

I know, I know… how are we talking about fall footwear when it feels like you’ve Swanton-bombed into a cast-iron skillet over an open fire?

But it’s September, and we feel obligated to at least help you bookmark some weather-appropriate footwear before you adjust your thermostat.

We’ve put together some of our favorite shoes to carry you from now through that stretch when the leaves start crunching beneath your outsoles.

From moc toes and trail shoes to chukkas and derbies, we’ve got the kicks to take you from morning miles to bonfires, and hopefully everywhere in between.

If you’ve been following along, we’ve already put together guides on:

  • Socks

  • Ecru Garms

  • Rugged Shirts

  • Bags

  • T-shirts

If you’re new to the guides, we drop one a week and the categories are always different. If you want access to these shopping guides for yourself or a loved one, you can subscribe here.

A few notes about these guides ❤️

  1. As always, if you’re looking for trendy shit on the cheap, this isn’t the best place to look. You need the right stuff, not more stuff.

  2. A lot of these recommendations tend to be medium to higher price point (though not always). If you’re looking for quality, affordable options, I always recommend thrifting what you can (like eBay, vinted, etc), or looking at options like Uniqlo.

    1. If you like these guides, share them with a homie, partner, family member, lover, or anyone who would appreciate it!


Moc Toes

Where to cop

  • Morjas The Camp Moc

  • Sebago Ranger Waxy Moc

  • Rancourt Baxter Ranger Moc

  • Quoddy Blucher Shoe

  • Studio Nicholson Guston Suede Shoe

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