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.
The Best Riding Boots for Fall
- Margaux The City Boot
- Toteme Square-Toe Leather Riding Boots
- Polo Ralph Lauren Vachetta Leather Riding Boot
- Larroudé Alexis Flat Boot In Brown Croc Leather
- Jimmy Choo Lawton Suede Boots
- Everlane Leather Knee-High City Boot
- Franco Sarto Franco Meyer Knee High Boot
- Loeffler Randall Indy Black Leather Tall Boot
- Sarah Flint Perfect Riding Boot 30
- Manolo Blahnik Luchino Black Calf Leather Knee High Boots
- Penelope Chilvers Inclement Long Tassel Boot
- Aquatalia Ricarda Leather Riding Boots
Margaux The City Boot
Margaux’s classic black leather riding boot might look simple, but it’s a wardrobe powerhouse. The rounded almond toe adds a touch of drama, while the 1.5-inch stacked leather heel adds height, but is still decidedly wearable for everyday, thanks to 5 mm of foam padding. The hidden interior zipper ensures you won’t struggle to pull these off at the end of a long day.
Toteme Square-Toe Leather Riding Boots
Toteme is known for its luxurious, minimalist pieces, and these tall riding boots are no different. A softly pointed upper leads to a square toe and an extended welt, with a subtle, under one-inch stacked heel. A strap at the collar adds unexpected dimension to the Italian-made leather boots.
Polo Ralph Lauren Vachetta Leather Riding Boot
It’s no surprise that Polo Ralph Lauren does a riding boot well—the brand is basically the unofficial uniform of horse girls worldwide. These cognac-colored, round-toe boots are accented with white stitching and finished off with a sturdy wooden heel and buckled strap.
Larroudé Alexis Flat Boot In Brown Croc Leather
Crafted in Brazil, this knee-high boot brings just the right amount of edge to your autumnal wardrobe. The embossed croc is unexpected yet surprisingly versatile, and the wider collar is not only flattering, but also convenient to pull on over a thicker jean or pant.
Jimmy Choo Lawton Suede Boots
Inspired by classic riding boots, Jimmy Choo’s suede Lawtons feature a round toe, low 1.5-inch heel and knotted leather straps around the ankle. The plush suede fabrication is a softer, more subdued alternative to the usual leather.
Everlane Leather Knee-High City Boot
Sleek yet sturdy, Everlane’s leather knee-high riding boots are the kind of shoes that end up as your fall and winter staple footwear. A softened square toe, two-inch heel and leather outsole are functional, but not boring.
Franco Sarto Franco Meyer Knee High Boot
These versatile brown leather boots have a flattering silhouette with room around the leg, with a zipper that goes all the way up to the top for easy wear.
Loeffler Randall Indy Black Leather Tall Boot
The ultimate sleek, day-to-night boots that effortlessly pulls double-time. Made from a comfortable yet structured calfskin leather, with an elongated almond toe and 1.5-inch block heel. For the days that start with an 8 a.m. coffee meeting and end with a much-deserved martini.
Sarah Flint Perfect Riding Boot 30
Add a classic shoe to your wardrobe with these brown knee-high riding boots, which have a slightly higher wooden heel, stretch paneling and happen to be up there with the most comfy options available.
Manolo Blahnik Luchino Black Calf Leather Knee High Boots
Does Manolo ever miss? There’s a reason the iconic designer remains a go-to for classic footwear—these black calf leather knee-high boots are a lesson in how to subtly modernize a traditional silhouette, thanks to a more relaxed fit and a rubber sole that doesn’t shy away from city puddles.
Penelope Chilvers Inclement Long Tassel Boot
These waterproof boots from Kate Middleton’s go-to English brand are made of weatherproof suede, with a rubber sole, and will have you ready for a weekend in the country—or just a rainy day strolling around the city. They come in both standard as well as a “generous” option that’s ideal for those seeking a wide-calf boot.
Aquatalia Ricarda Leather Riding Boots
For a classic pair of riding boots that also give you a bit of extra height, try these brown leather shoes. The low block heel makes them a bit more of a dressy boot, while the stretch paneling makes them easy to slip on and off.