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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