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Trending Ankle Boots

Fall Is Near—Shop These 18 Ankle Boots To Prepare Your Shoe Game

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The biggest sign that fall is back doesn’t lie in the changing leaves or dropping temperatures. While those are effective indicators, there is one uncanny detail that makes it abundantly clear that the seasons have shifted: footwear. Or more specifically, ankle boots. They’re the quintessential fall shoe—perfect for tailgates, coffee dates, and enjoying the cool weather. Once you spot these babies strolling down the street, be prepared for autumn because it’s coming quickly.

As fall is one of the busiest seasons, having a comfortable shoe with a touch of added flair is especially important. After all, isn’t cozy and fun what this period is all about? Plus, there are tons of colors and styles to choose from, so you can add your own spin to the classic booties. This season, expect to see a lot of suede in a range of silhouettes, loafer-inspired ankle boots (take a look at that adorable Gucci style below), chunky soles, curved heels, and toes that range from ultra-pointy to square. Keep scrolling for a guide to the ankle boots trending big right now.

All products and deals are sourced by the Rank & Style team using data and expert insights. If you shop through our links, we may earn a commission—at no extra cost to you.

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August 18, 2025

Written By:Beth Zerdecki

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Image credits: madewell

madewell

Madewell The Dimes Kitten-Heel Boot

$218

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By Anthropologie Western Ankle Boots

$190

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Coach Sculpted C Leather Booties

$285

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Matisse Cleo Pointed Toe Bootie

$238

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Stuart Weitzman Soluxe Hudson Chukka Boot

$650

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Frye Campus Chelsea Boots

$358

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Alohas West Cape Burgundy Wine Boots

$310

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Veronica Beard Lisa 70mm Pointed Toe Bootie

$495

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Staud Wally Square Toe Ankle Boots

$495

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FP Collection Faster Horses Filigree Boots

$248

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Alohas Lizzie Black Leather Ankle Boots

$320

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UGG Classic Ultra Mini Shearling Booties

$160

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Schutz Maryann Curve Boots

$198

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Gucci Sylke Luxury Booties

$1320

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Jeffrey Campbell Waylon-Lo Square-Toe Western Ankle Boots

$345

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Blondo Marcie Waterproof Bootie

$150

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Dr. Martens Jadon Lace-Up Boots

$210

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Sorel Joan Chelsea Boots

$170

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