Chinese Laundry Women's Riding Hood Ankle Boot

Sleek, sixties style define the Jefferson booties by Report. The classic ankle boot silhouette features smooth suede for a look that flirts with retro.

Whether it's the pretty polka dots, the cute red wedge, or the darling heart cutouts, you're bound to fall in love with something on the Love Rachel Antonoff Danita platform wedges by GH Bass Shoes.

Ride high in the saddle with these sky-high boots from Naturalizer. The Ora features a wide-calf, pull-on silhouette.

Polished and ready for the race. The Marni riding boots by XOXO feature a classic silhouette with lace-up detail at back.