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Fall/Winter Shoes Part 1

The boots and winter shoes of the season + how to wear them.

Ali Pew's avatar
Ali Pew
Nov 19, 2025
∙ Paid

The question on everyone’s mind: What shoes do I wear right now?

A boot is the obvious choice once it’s cold. But lately, especially before it gets too cold, I’ve been more into a sock-and-shoe option. It just feels more interesting right now.

I broke everything down—what I’m wearing and how to wear it. The edit got so long that it’s now a two-part series. Today covers boot shapes (almond, pointed, square), the best lace-ups, and what to wear when it snows. Next post we will get into cozy pairs for home and snow, and a few for night.

Cowboy

References: Khaite boots with a perfect jean shape over them, Khaite Resort 2026 is exactly how I want to wear this boot (but also with a trouser), A Emery boots with what I can only imagine are High Sport Pants.

The clean minimalist in me likes this styled simply but with a fashion edge. I really like a pant (jean or trouser) pulled over a cowboy boot. I also love the idea of wearing them with a great suit (jacket and pant here). To get that Khaite resort look with this style of boot, I’d wear them with this perfect jean and a great leather jacket. This Toteme pony hair small bag would be cute with it, too.

The below are more of a true cowboy boot in cut and detail. These are my favorites that still feel wearable without looking like you’re headed to a rodeo. All of these are narrower at the top, so pants can go over without bunching.

Prada Boot, Aeyde Boot, Partlow Boot

If you can’t quite go there, go with a cowboy-leaning style. Simple, cleaner, and a little more Saint Laurent, less Lucchese.

Khaite Boot, A Emery Boot, Le Monde Beryl Boot- I am into this wedge shape.

Lace Ups

References: Celine Spring 2026, Bally shoes styled with a perfect color combo, and W Mag shows us how to do a little sporty but keep it minimal

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