Slip into this adorable leather ankle boot with a plush faux-shearling lining and a soft, cushioned insole.
Nera, $129; www.EasySpirit.com
O's creative director, Adam Glassman, lists his picks for the best over-the-knee boots this season.
Our top picks for knee boots this season.
Our top picks for over-the-knee boots this season.
Swap out clunky winter boots for a sleek shearling pair.