The Enduring Appeal of the Riding Boot, From Stable to Sidewalk

The riding boot’s origins are right out of the horse girl arena, but over the years, the knee-high boot has firmly cemented its place in the realm of mainstream fashion—even for those who aren’t interested in spending time in stables or talking about equestrian lore. And while fall shoe trends come and go, the riding boot has a certain timeless allure. After all, if a shoe can emerge from the somewhat terrifying depths of peak millennial fashion of the early 2010s (I’m talking low-rise skinny jeans and some iteration of an infinity scarf, maybe even with a beanie—and yes, I am, in fact, speaking from personal experience) relatively unscathed, then it can do anything.

The traditional riding boot—that is, the most traditional version not explicitly designed for riders—is crafted from brown or black leather and hits just below the knee, with a low block heel. These classic styles embrace the shoe’s innately preppy, Ralph Lauren-girl nature, but the beauty of the riding boot is that it doesn’t lean too far toward one particular aesthetic—it’s all in how you put the outfit together.

Indeed, the sheer versatility of the riding boot is surely a large reason why the shoe has stood the test of time. This knee-high boot has some serious range, whether you want to wear yours with a crisp pair of jeans and a turtleneck, or perhaps with a flouncy dress or oversized sweater. Select a higher heel if you prefer some extra height, or stick with the standard one-inch block heel if that’s more your vibe. There are also more unexpected interpretations of the riding boot, whether it’s a bold colorway, unique fabrication or whimsical detailing. Below, peruse the season’s best riding boots, from classic leather to croc-embossed styles.