11 Best Ankle Booties

As I type this, I’m donning my all-time favorite pair of winter boots — classic black leather riding boots that hit just below the knee. I think they’ve earned their title, seeing as this is my sixth winter with them (impressive, right?), but there’s always room for a new pair or two come November. Since there’s been so much boot talk around the office — which seems to be commonplace this time of year — we thought we’d devote today’s 10 Best (+1) to rounding up some of our favorite ankle booties. You all know, the possibilities are endless when it comes to heel height, color, material, and shape, so we’d love for you to weigh in on which pair you’ve got your sights on this season!

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Dynamite Ankle Bootie from Corso Corso

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Kiver Ankle Bootie from H by Hudson

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Chelsea Leopard Rain Boots from J. Crew

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Elasticated Panel Ankle Boots from Tod’s

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Caribou Boot from Sorel

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Adele Glossy Leather Ankle Boots from J. Crew

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Gigi Open-Toe Leather Ankle Boot from Loeffler Randall

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Metallic Linen Desert Wedge Boot from TOMS

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Micro-Studded Flat Leather Booties from ZARA

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Bordeau Leather Ankle Boots from Bronx

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Tan Leather Ridge Flat Ankle Boots from Dune