Circus by Sam Edelman Parker Boots
About as classic as they come, these black riding boots have those just-right equestrian touches (note the buckle and arched tops) that mean they’ll never go out of style. Also available in brown suede.
To buy: $55, 6pm.com.
Rampage Vally Tall Boots
Looking for a pair that’s a little less prim, a little more laid-back? Try this rugged knee-high style on for size. Burnished brown faux leather gives off a relaxed vibe, while detailed ankle straps (complete with decorative stitching and hardware) offer tons of visual interest. Also available in black.
To buy: $60, amazon.com.
ASOS Karmen Wide Fit Pointed Over the Knee Boots
Clothing comes in different sizes to fit differently-sized people, so over-the-knee boots—which cover nearly half of your body—should, too… right? We love that ASOS offers several of their most popular options, like this one, in wider fits as well.
To buy: $83, asos.com.
Banana Republic Vail Riding Boot
It’s the little things. Subtle details like the buckle at the top of these boots make them look super luxe. On a practical level, a side zipper means they’re easy to get on and off, and the lug sole offers great traction in wintery conditions. Also available in black.
To buy: $198, bananarepublic.com.
Kendall and Kylie Fedra Over the Knee Boots
The best part of this over-the-knee pair? It’s not the sleek, leg-elongating pointed shape or the cool (not to mention sturdy) half-wedge heel (although those details are pretty great). It’s the unexpected gray hue, which works with any color you wear them with and looks equally good dressed up or down.
To buy: $225, bloomingdales.com.
Boohoo Lucy Flat Tie-Back Over the Knee Boot
What’s better than a flat, over-the-knee boot? One that rings in well under $100, like this style. Adjustable ties at the tops keep them from slouching or slipping down. Also available in black.
To buy: $68, boohoo.com.
Chinese Laundry Set in Stone Boots
This pair has an unusual layered look that sets them apart from a sea of black boots. Wear them with leggings and a tunic for an effortless, polished weekend vibe. Also available in cognac.
To buy: $80, chineselaundry.com.