The 20 Best Over-the-Knee Boots for Conquering Transeasonal Style

For those searching for a practical boot with a side of drama, nothing tops the over-the-knee boot. Smart and seductive, the silhouette is the must-have for any au courant shopper—thanks, in part, to its structured shape and various texture options. Together, these make it a seasonless shoe that you can wear come rain, wind, snow, or sun. Once synonymous with sensual characters like Vivian Ward in Pretty Woman or Jane Smith in Mr. & Mrs. Smith, the original over-the-knee boot has grown legs; it has evolved for the modern wearer. 

Last season, beloved brands Stuart Weitzman and Bottega Veneta released a trove of utilitarian versions that featured terrain-gripping lug soles and waterproof exteriors. Alternatively, for Fall/Winter 2021, designers returned to the aesthetic that originally defined the boot: eroticism. Paired with our hankering for a late-night rendezvous or three, these newer styles feel charged with the high-octane glamour attributed to the early ’70s. (After all, Studio 54 fixtures were known to don over-the-knee stompers every weekend.)