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Fall/Winter Shoes Part 2

For inside, outside, and somewhere in between.

Ali Pew's avatar
Ali Pew
Nov 21, 2025
∙ Paid

An encore to Wednesday’s post on the winter shoe. This round is less about categories and more about moments. The boot I always reach for. A lounge shoe that’s too good to leave inside. An evening shoe that adds just enough interest to an otherwise repeat outfit.

Squared Off Toe Boot

References: Hermes, Elizabeth Hurley, Jil Sander

I can’t not have this category of boot in my closet. Maybe it’s the ‘90s nostalgia, or maybe it’s just the most timeless and wearable style. They look great with a wide leg pant, cool with jeans, elongate the leg with dresses or skirts. This is never a boot I’m looking for, but I always end up wearing. And the tiny heel on most of these gives you just a little lift for the look of a longer leg without sacrificing comfort. Highly recommend with Attersee utility trousers (my wardrobe mvp).

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