You Can Bet on Riding Boots This Winter

What makes for a perfect boot? For one, it should be versatile enough to fit into your fall wardrobe, pairing well with everything from androgynous rugby shirts to preppy skorts. Secondly, it’s got to be easy to slip into and stay comfy all day long. And in a perfect world, it should be sturdy, snug and practical enough for you to effortlessly leap on the back of a horse and trot away from unsavoury situations. Riding boots do it all.

Where have we seen riding boots on the runways?

The Fall 2024 collections were peppered with the equestrian-inspired aesthetic, from Gucci’s olive green offerings to Miu Miu‘s slouchy iterations. Following that styling success, the Spring 2025 runways have only continued to favour this type of footwear. Models stomped with chunky black boots at Vaquera (below), while Prada put a retro spin on the design through a lacquered burnt orange wash.

Plus, judging from the street style outside the shows, the craze is only going to continue.

How to style riding boots now

If you’re looking for an edgy statement, opt for a pair festooned with buckles. Hardware-heavy knee-highs with a hint of a biker boot vibe bring a punch of punk to every outfit, especially when styled with baggy, oversized Bermuda shorts and tights. (Trust us.)

For a playful twist on menswear staples, opt for a minimal pair and wear alongside an oversized blazer. Here, the accessories can be even more eventful. For instance, adorn your outfit wildy with headbands, sunglasses and colourful gloves. As a result, you’ll have the perfect mix of professional, utilitarian and sharp streetwear.

Alternatively, lean into the Wild West styling-wise, and pair your clunky boots with a dainty floral maxi skirt. The outcome is an ultra-intentional meshing of fashion codes and an expert execution of personal style. You see, at their best, riding boots can be the conduit for outfit experimentation all season long.

The best riding boots to shop now

Reformation Nancy knee boot

Pictured in espresso leather, these chocolate-coloured riding boots add some warm dimension to round out darkened fall ensembles. With an easy-to-use side zipper, a subtle black heel and polished stitching throughout, they bring contemporary chicness to the classic Western style. Plus, the round toe silhouette gives them an extra elevated finish.

Steve Madden Rockyy white leather boots

Festooned with buckles and boasting a brindled white shade, these riding boots offer utilitarian style with an edgy twist. The smooth leather upper gives it that well-worn finish, white the durable synthetic footbed guarantees that they’ll last. Currently on sale, this fan favourite pick is the perfect way to infuse some fun into your cold-weather fashion routine.

Vagabond Eyra tall boots

Thanks to the severe square heel, exaggerated stitching and chunky block heel, Vagabond’s riding boots bring modern-day coolness to the riding boot game. Available in a faded brown, they capture the moodiness of fall, with pull-on shafts for an easy slip-on experience. Pair with knee-high socks for an academic edge.

Aldo Loreina riding boot

With a luxe brown finish and sleek statement top buckle, these chic boots boast a widening shaft reminiscent of an equestrian’s uniform. They also deliver on comfort, thanks to the smooth leather upper, grip rubber sole and signature pillow walk padded insoles. For the minimalists with a taste for Mary Kate and Ashley dressing, they also come in black.

Franco Sarto Meyer boot

Crafted from hand-finished leather, these reddish brown boots are equal parts vintage-inspired and timeless. With a rustic wooden heel, a slim almond-toe silhouette and intricate stitching throughout, they’re designed to fit well without compromising style. Because they are available in 11 shades and a variety of calf-widths, these palatably priced boots are a top-rated pick.

Sam Edelman Penny leather boot

A classic black riding boot with a refined finish, these chic Sam Edelman riding boots are designed to be lived in. The chic craftsmanship is an ode to equestrian codes — from the curve of the footbed to the pull-on straps accentuated with vintage-style buttons. As a result, these pair perfectly with other minimal basics like a trustee black skirt and a vest.

Dr. Scholl’s brilliance riding boots

You can’t go wrong with comfort and style. For a seamless blend of both, we turn to heritage footwear brand Dr. Scholl’s. Pictured in a rich whiskey shade, these faux-leather boots evoke the real supple fabric with a slight worn-in texture and buttery smooth lining. Because they’re made of recycled materials, they’re also a sustainably-minded pick.

Asos Raid Rosenna riding knee boots

Nothing turns heads like a good pair of glossy boots. This design combines the classic riding silhouette of a wide-shaft boot with the feminine polish of glazed French-girl footwear. Unlike your typical knee-high, these don’t hug the leg. Instead, they stay oversized and roomy, promising an even more playful styling experience. Our suggestion? A pleated mini skirt and button-down for an elevated collegiate ensemble.