One of the most-asked questions I get is: which ankle boots are we wearing for fall?! The right boot goes a long way in creating elevated fall outfits. Here are my picks for 2026. You're looking for high shafts and a long instep. Steve Madden Define boot 5.5 Steve Madden Zami bootie Staud Wally ankle boot Staud Wally heeled ankle boot 35 Vince Hailey boot 5.5 Madewell Calli Ankle boot Madewell Paisley ankle boot J.Crew Sylvie ankle boot Sezane Garance ankle boot Dolce Vita tartine bootie

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Steve Madden Define Block Heel Bootie (Women) | Nordstrom | Nordstrom
STAUD Wally Snip Toe Bootie in Espresso at Nordstrom, Size 11Us | Nordstrom
STAUD Wally Ankle Boot (Women) | Nordstrom | Nordstrom
The Paisley Ankle Boot | Madewell
The Calli Ankle Boot | Madewell
Garance Ankle Boots | Sezane Paris - US
Sylvie ankle boots in leather | J. Crew US
Tarine Booties Dk Brown Nubuck | DolceVita.com
STAUD Wally Ankle Boots Black 38 | Shopbop
Vince Hailey Bootie in Elmwood Suede at Nordstrom, Size 9 | Nordstrom
Steve Madden Zami Leather Bootie in Black Leather at Nordstrom, Size 8.5 | Nordstrom