Whoorl

Whoorl

The Fall Boot Report

Boot season is upon us and I couldn't be happier.

Sarah James's avatar
Sarah James
Oct 28, 2025
∙ Paid

Every October, I feel that familiar little spark of excitement when the air shifts and I finally get to pull my boots out again. Boots are my FAVORITE. They create such cohesion in my outfits and usually eradicate the issue of bare ankles. (Socks or no socks? Who cares?)

I’ve been keeping an eye on what’s out there this season, and the good news is that the classics still reign. Sleek ankle boots, tall structured pairs, and just enough western-inspired details to keep things interesting.

Here’s what I’m loving right now.

1. The Everyday Ankle Boot

If I had to choose one pair to live in, it would be a block-heeled ankle boot in smooth leather. Or suede. Ooh, that’s tough a choice, actually. My favorite luxury pair from this season are these Gianvito Rossi gems. I’m telling you, that exact shade of brown is so hard to come by. I also love and wear the hell out of my Toteme suede booties.

However, year after year, I’m always impressed with the affordable J. Crew options. The Stevie boots are always excellent (I have black and dark brown), and I’m also loving this pair. (30% off J. Crew right now!)

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