28 Ankle Boots to Buy Now and Wear Forever

By Sara HolzmanMarina LiaoLaura Lajiness Kaupke

You’ll find at least one pair of ankle boots in every woman’s closet, and for good reason. Yes, you can sport them in the summer, ‘90s-style, underneath your cottagecore frock or your slinky slip dress. But ankle boots really take center stage in the fall and winter, when temperatures begin to drop and denim becomes a mainstay. Whether you favor functional silhouettes engineered for the outdoors, cozy interiors, or refined leather styles, there’s a heel height, sole construction, and bevy of embellishments for just about any fashion play. So consider investing in a pair (or two) of ankle boots that you can test-drive now and live in year-round. We’ve hand-picked our favorites.

Gia Borghini Marte Leather Ankle Boots

Chunky rubber soles are the look of the moment—offset this pair with a flowing midi dress.