How to Style Riding Boots This Fall

Trending codes of modern prep are equipping fashion’s beloved horse girl with all of its frills and finery. From tailored barn jackets to silk neck scarves, motifs of countryside living found their stride on the fall 2025 runways. For those keen to embrace the look, if not the actual lifestyle, what better entry point than the linchpin of it all? The leather riding boot.

Vogue’s Favorite Equestrian-Inspired Boots

Seen across the fall 2025 runways, the riding boot reemerges as both a classic and contemporary style leading the fall boot trends. Think buckled, flat, or stacked heeled variations that blend functionality with refinement–perfect for the city commuter or a jaunty to the countryside. This season is about channeling your inner horse girl—riding lessons not required.

Below, shop the best equestrian-inspired boots of the season and discover exactly how to style them for a look that’s equal parts heritage and modern polish.

Photo: Isidore Montag / Gorunway.com

The Pleated Trouser and Shearling Jacket

True to the sport’s roots, tuck houndstooth trousers into a pair of leather equestrian boots. Layer on Banana Republic’s shearling lined leather jacket for a nod to Burberry’s styling, then round out with statement making Gucci frames for the perfect mix of heritage and contemporary style.

Photo: Courtesy of Ralph Lauren / Gorunway.com

The Plaid Dress and Brown Accessories

The ultimate country-coded print takes center stage with Polo Ralph Lauren’s plaid midi dress. Ground the look with Brunello Cuncinelli’s riding boots in a rich chocolatey brown, then add a touch of sophistication and structure with Coach’s empire carryall and Nili Lotan’s gold-buckled belt.

Photo: Daniele Oberrauch / Gorunway.com

The Leather Short and Long Jacket Duo

Riding boots can be the focus, as shown here with mini shorts and a sweep coat. It’s a lesson in proportions that works surprisingly well no matter your tall boot of choice. A satin tie top adds a refinished finish.

Photo: Umberto Fratini / Gorunway.com

The Maxi Skirt With a Pop of Red

Take inspiration from Tory Burch’s fall 2025 runway for the ultimate fall color combo: red and brown. Pair the rich, mocha tones of Tory Burch’s twisted riding boots and Simkhai’s Jamie dress with the vibrant pop of Magda Butrym’s belted jacket and Givenchy’s Nano Voyou bag for a refined blend of equestrian elegance and utilitarian edge.

Photo: Daniele Oberrauch / Gorunway.com

The Midnight Trench

Does it get more classic than a trench coat and riding boots? We think not. The power pairing gets a modern finish with Jil Sander’s commanding riding boots and Alaïa’s sculptural Le Click bag–a masterclass in enduring style.

Photo: Daniele Oberrauch / Gorunway.com

The Personality Collar and Culottes

For riding inspiration rooted in Elizabethan elegance, look to Dior’s fall 2025 collection. Style Church’s lace-up riding boots with Loulou de Saison’s culottes and a statement collared shirt for a sharp update. Add flair by fashioning J.Crew’s silk dotted scarf as a necktie.

Photo: Courtesy of Loro Piana / Gorunway.com

The Slim Pants and Layered Utility Jackets

Loro Piana takes the preppy riding aesthetic to new heights. Take cues from the collection’s look book and pair Gucci’s Horsebit boots with Banana Republic’s white trousers for a crisp foundation. To channel the modern prep vibe, layer on utility-inspired outerwear–the ideal pairing found in Loro Piana’s khaki shell and Chloé’s buckled vest.

Photo: Courtesy of Ralph Lauren / Gorunway.com

The White Lace Dress and Cinched Belt

For a dose of romance, look to Ralph Lauren’s white lace number for direction. Dôen’s Orelie dress gets a modern upgrade with Khaite’s cinched waist belt and Staud’s sharp riding boots. Finish with Chanel’s Premiére Édition Originale watch–a timeless accent that carries you seamlessly from day-to-night.

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