E! Illustration/ Reformation, NordstromThere’s no question that boots are the ultimate autumn shoe. The question every year is: what boot style is going to trend this fall. The answer? Riding boots.
That’s right, in 2026, we’re having a horse girl fall. From a Princess Diana-inspired countryside outfit to Kendall Jenner‘s equestrian-chic ensembles, you’re about to see riding boots all over your fall feed.
- Most Classic Design: Sam Edelman Penny Riding Boot
- Trendy & Comfortable: Dr. Scholl’s Women’s Joplin Wide Calf Tall Boot
- (now $135.15, was $375)
The heritage style is defined by a knee-high silhouette, sleek leather uppers, and a (usually) flat heel. Typically seen in rich hues like chocolate brown, deep burgundy, distressed tan, and classic black, riding boots provide a quiet luxury feel that gives “IYKYK” energy.
They complement the skinny jean comeback as much as they do a textured tights and a mini dress combo. Basically, riding boots are the versatile shoe your fall wardrobe is lacking—and you can shop our favorites below.
Michael Kors Royce Riding Boot
Designer boots for 72% off? Yes, please! This zip-up Michael Kors pair is sleek, shiny, and boasts a subtle version of the brand’s signature gold logo.
Sam Edelman Penny Riding Boot
These boots are giving equestrian elegance. Tall and streamlined with a round toe, they really channel that, “just came from the barn” feel.
Crown Vintage Feya Boot
Get the Frye look for less with these knee-high boots with a hint of Western flair. Featuring a half-zipper closure, they also come in black.
ASOS DESIGN Callahan Leather Riding Boots
These almond toe leather boots have an asymmetrical leg openings for added interest and a pull-on design for easy on and easy off.
Steve Madden Sady Boot
Buckle accents adorn the base and top of these tall boots, giving them a subtle motorcycle edge. Available in classic brown or black, they’re made from soft, rich leather.
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