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

Kiver Ankle Bootie from H by Hudson

Chelsea Leopard Rain Boots from J. Crew

Elasticated Panel Ankle Boots from Tod’s

Caribou Boot from Sorel

Adele Glossy Leather Ankle Boots from J. Crew

Gigi Open-Toe Leather Ankle Boot from Loeffler Randall

Metallic Linen Desert Wedge Boot from TOMS

Micro-Studded Flat Leather Booties from ZARA

Bordeau Leather Ankle Boots from Bronx

Tan Leather Ridge Flat Ankle Boots from Dune

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