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Fall Guide to Transitional Jackets

A guide to shopping some of our favorite mid-layering pieces right now.

Leon Hedgepeth and Sprezza
Sep 10, 2026
∙ Paid

I woke up to a mid-60s-degree morning the other day and was happy to finally lint-roll a few mid-layering pieces for the season.

It’s a month-and-a-half window at best, but transitional dressing is a godsend. Maybe you want to throw on an overshirt over your tees, or tuck in that “big” Oxford shirt and wear it with a tattered denim jacket you haggled for at a 7 a.m. flea market.

For the next few weeks, now’s the time to start lightweight layering before bringing out the heavy coats.

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

  • Fall Footwear

  • Socks

  • Ecru Garms

  • Rugged Shirts

  • Bags

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!

Overshirts

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