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The 8 Best Riding Boots

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MILAN, ITALY - FEBRUARY 22: A guest wears rings, a black leather jacket with black suede sleeves , white leather pants, black riding boots, a red woven leather handbag, outside MSGM, during Milan Fashion Week Fall/Winter 2020-2021 on February 22, 2020 in Milan, Italy. (Photo by Edward Berthelot/Getty Images)

Riding boots are a wardrobe staple that will never go out of style — so even if you’ve never set foot in a stable, it’s a good idea to invest in a comfortable pair that will last you through several seasons (or even decades) of regular wear. The best riding boots for actual horse riding have small, 1-inch heels and durable leather uppers to protect your calves from rubbing against a saddle, but if you’re simply going for the equestrian look, a knee-high boot with an asymmetrical topline and stable-chic accents will be great for pulling together all sorts of outfits.

Because of their versatility, riding boots can be mixed and matched with other pieces to help transition your wardrobe from winter to spring and summer to fall, so they're a rare pair of boots you can wear throughout most of the year. Traditional knee-high riding boots have a simple, timeless design that usually works well with everything from jeans and leggings to skirts and dresses. More fashion-forward riding boots tend to feature details like quilted stitching or extra buckles across the ankle to add a touch of personality.

Here are some of the best riding boots for women, from Western-chic styles to pairs you can actually wear horseback riding, all conveniently available on Amazon Fashion.

A Pair Of Classic, Two-Toned Equestrian Boots

These Tommy Hillfiger riding boots are the epitome of classic, equestrian-chic style. The uppers are made from vegan-friendly faux leather, and the handy, zippered closures make these easy to put on and take off. Meanwhile, the discreet, H-logo buckles at the top elevate the look without feeling overly ornate. If you don't love the two-tone style, these are also available in both solid black and brown.

  • Available colors: 3
  • Available sizes: 5 — 12

These Simple Black Boots With Subtle Quilted Details

These classic black riding boots have quilted back panels and a soft interior lining that will keep your legs warm in cooler weather. They're made from 100% synthetic materials, so they’re not overly delicate — you can wear these out and about without worrying about damaging the leather. Other highlights include a wide, 15.6-inch opening at the top and a full-length zipper closure to make putting them on (and taking them off) a breeze. If you find that they’re a bit too loose, note that you can adjust the fit using the buckles at the ankles and the knees.

  • Available colors: 8
  • Available sizes: 6 — 11

A Pair Of Western-Chic Frye Boots

These genuine leather riding boots from Frye look like they’d blend right into a horse-riding scene from a period drama. The asymmetric topline of the boot is similar to what you’d see in a traditional equestrian boot, and the distressed leather finish gives them a timeless look. The boots are contoured at the ankle for additional support, while small leather snaps at the top and bottom keep the most important parts of the zipper protected. Choose from 16 gorgeous, rugged-chic shades of black, gray, and brown.

  • Available colors: 16
  • Available sizes: 5 — 10

Some Super-Comfy Riding Boots With Buckle Details

These boots from Naturalizer have an elastic back and asymmetrical topline for a super-comfortable fit and stylish silhouette. The buckle details give these a more fashion-forward look, and their uppers are made from soft, full-grain leather. Amazon reviewers report that these boots are great for those with larger calves, as these have a wider opening circumference and easily zip closed without snagging.

  • Available colors: 7
  • Available sizes: 4 — 12

A Pair Of Sam Edelman Boots With A Low Stacked Heel

These boots from Sam Edelman have beautiful leather uppers that look perfectly worn-in right out of the box. The antiqued button details on the snaps also add to the vintage charm, and the stacked, 1.25-inch heel is slightly taller than average, but still comfortable enough for all-day wear.

  • Available colors: 4
  • Available sizes: 4 — 12

These Traditional Riding Boots You Can Style So Many Ways

If you’re looking for a pair of classic riding boots you can wear to the stable and beyond, these TuffRider boots are a great option. They feature genuine leather uppers and memory foam insoles for comfort in and out of the saddle. You can also choose a dedicated calf size on these boots to ensure that they fit like a second skin without any gaps or pinching. Other practical and elegant-looking features include spur rests that prevent English-style spurs from sliding down the boot, and leather snap closures at the tops and ankles.

  • Available colors: 1
  • Available sizes 6 — 11 (available in X-Slim, Slim, Regular, and Wide shapes)

A Pair Of Classic Black Boots With A 2-Inch Heel

Prefer a classic riding boot style with just a little more height? Then these boots from Rampage are a great (and super budget-friendly) pick. The 2-inch stacked heel is comfortable enough for longer periods of wear, and the synthetic uppers are vegan-friendly and low maintenance. The interior zippers and pull tabs make putting these boots on effortless, as well.

  • Available colors: 6
  • Available sizes: 6 — 11

These Minimalist-Chic Boots That Have Just Enough Stretch

These chestnut-toned riding boots from Cole Haan are great if you find most tall boots too snug or restricting. They have a stretchy, elastic back that ensures a perfect fit that moves with you, and a soft interior lining. They're also a great choice for those who prefer a flatter heel. Amazon reviewers report that these boots fit great for those with wider calves, and their minimalist profile with few accessories provides a classic, clean-looking silhouette.

Also Great: A Western Style Riding Boot You Can Wear With Any Outfit

If you're after a more Western-inspired equestrian look but don't want to go with a full-length cowboy boot, these Western boots from Ariat offer great support and finely detailed stitching. Amazon reviewers report that these boots are tough enough to be comfortable for long days in the saddle, but they're also perfect for styling with jeans, dresses, and maxi skirts. They come in tons of colors and styles, so it’ll be easy to find a pair to suit any aesthetic.

  • Available colors: 24
  • Available sizes: 5.5 — 11