It’s Time to Embrace the Riding Boot—Here’s How to Wear the Wardrobe Essential

You can't go wrong with a timeless riding boot.

It’s Time to Embrace the Riding Boot—Here’s How to Wear the Wardrobe Essential
woman wearing black Celine shades, a grey Toteme jacket, a Maison Margiela bag and black Flattered boots
You can’t go wrong with a classic riding boot. Getty Images

Autumn is coming up, which means it’s officially time to stow away those sandals, maillots and all things linen and bring out your favorite cozy knits, textured trousers and those boots you’ve been missing for the past few months. A cool girl lace-up combat boot, classic Chelsea short boot and a sturdy lug sole ankle boot are always good options, but let’s not forget about the timeless allure of the riding boot.

The equestrian-inspired shoe might have origins in the horse girl arena, but has since firmly cemented its place within mainstream fashion. While an adoration of all things horseback riding isn’t a prerequisite for a love of the riding boot, the rise of the horse girl aesthetic has surely contributed to the ever-growing appeal of this particular shoe.

Riding boots are traditionally knee-high and made of leather, with a subtle, barely-there low block heel. You can’t go wrong with a classic black leather riding boot, but there are also plenty of more unexpected, high-fashion interpretations of the look, whether it’s a bold colorway, a unique embossed material or a dramatic heel. A riding boot adds an effortless elegance to any look; they’re preppy but no overly so, and bring a more put-together vibe to your ensemble. They’re a more classic and wearable option to the trending cowboy boot, though there are also plenty of western-inspired riding boots.

The Duke And Duchess Of Cambridge Visit Ireland - Day Two
Kate Middleton is a big fan of the classic riding boot. WireImage

You can embrace the equestrian trend and pair the boots with your favorite denim and a tailored button-down shirt, throw them on with a feminine frock for a seamless transitional look, or wear them with tucked-in skinny jeans à la Kate Middleton and noted horse girl Gigi Hadid. Below, take a look at our favorite riding boots that you’ll want to add to your shopping cart ASAP.

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The Best Riding Boots for Every Style Preference

The best women’s riding boots.

  • Gucci.

    Gucci Zelda Riding Boot

    Go for the full equestrian boot look in these Gucci riding boots.

    $2,050, Shop Now
  • Franco Sarto.

    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.

    $250, Shop Now
  • Toteme Square-Toe Leather Riding Boots

    Toteme Square-Toe Leather Riding Boots

    Toteme is known for their luxe minimalist pieces, like these chic tall riding boots with a square toe, stacked heel and decorative strap.

    $1,200, Shop Now
  • Polo Ralph Lauren.

    Polo Ralph Lauren Vachetta Leather Riding Boot

    Of course Polo Ralph Lauren is behind the ultimate riding boot; these cognac-colored round-toe shoes have subtle white stitching, a wooden heel and buckled strap.

    $698, Shop Now
  • Proenza Schouler.

    Proenza Schouler Pipe Riding Boots

    Proenza Schouler’s splurge-worthy, timeless black riding boots have a flattering v-cut topline, which also adds to the ease of getting them on and off. The treaded rubber outsole provides extra traction for less slippage, too.

    $1,295, Shop Now
  • Chloé Mallo Leather Knee-High Boots

    Chloé Mallo Leather Knee-High Boots

    These boots are inspired by a classic riding style, because you don’t have to actually get onto a horse to embrace the riding gear trend. These leather boots have chunky heel and western boot-influenced stitching.

    $1,590, Shop Now
  • Loro Piana.

    Loro Piana Decker Boots

    Are these Loro Piana tall boots an utterly extravagant purchase? Yes, they are, but if you want to make a major investment in a high-quality forever shoe, they’re surely worth the consideration. These knee-high, equestrian-inspired boots are made of the softest camel-hued leather, with a wider fit that’s incredibly flattering.

    $2,700, Shop Now
  • Sarah Flint.

    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.

    $995, Shop Now
  • Khaite.

    Khaite Derby Riding Boot

    Khaite’s signature minimalism is at its best with these pull-on black calfskin boots.

    $1,460, Shop Now
  • Penelope Chilvers Inclement Long Tassel Boot
    Penelope Chilvers.

    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 county—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.

    $725, Shop Now
  • Aquatalia Ricarda Leather Riding Boots

    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.

    $625, Shop Now
It’s Time to Embrace the Riding Boot—Here’s How to Wear the Wardrobe Essential