Fab Five: Giddy Up! 5 stylish riding boots to wear this winter


After a few seasons of pretty-hard-to-wear, love-or-loathe-them cowboy boots, it’s finally time for riding boots to have their turn in the style spotlight.

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All fashion trends are cyclical. And after a few seasons of pretty-hard-to-wear, love-or-loathe-them cowboy boots, it’s finally time for riding boots to have their turn in the style spotlight.

You’d be hard-pressed to find a more elegant, sophisticated boot style — and one so versatile, too.

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Whether you wear them for work, on the weekend, or actually for, well, riding, here are five stylish pairs to consider this winter.

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Anine Bing 'Kari' boots, $967.50 at Revolve, revolveclothing.com.

SMOOTH OPERATOR

Riding boot purists would say that a true riding boot must be made from smooth, high-quality leather — just like these Anine Bing “Kari” pair. Even if you never step foot into a dressage arena, you’ll appreciate the polished look afforded by the polished leather of these boots. They’re the perfect pairing for dresses, skirts and all of your more formal looks this fall.

Revolve, revolveclothing.com | $967.50

Michael Michael Kors 'Ridley' logo jacquard boot, $328 ($199) at Michael Kors, michaelkors.com.

GO LOGO

In addition to a short, block heel and knee-high length, riding boots almost always feature a snug fit around the calf. For a pair that fits this brief but offers something a little extra, consider this logo jacquard “Ridley” pair by Michael Michael Kors. The back woven panel features the brand’s initials, while the rubber tread sole adds a bit of practicality to this fashion-forward take on a classic.

Michael Kors, michaelmichaelkors.com | $328 ($199)

Jil Sander tan asymmetric boots, $1850 at SSENSE, ssense.com.

A SIMPLE MATTER

While some riding boots have decorative buckles or straps, there’s something just gorgeous about classic simplicity. Case in point: This asymmetric pair by Jil Sander. We’re partial to their pull-on silhouette — no zippers disturbing those smooth lines, curved, architectural tops, and buffed leather in the perfect, wear-with-everything shade of tan.

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SSENSE, ssense.com | $1,850

'Eterimma' boot, $220 at Aldo, aldoshoes.com.

RUSSETT BEAUTY

If you’re looking for a riding boot that really channels that horseback spirit, this “Eterimma” is an excellent option. The cross-leather straps and ornamental loop detail at the ankle evoke everything we love about equestrian culture, while the soles feature Aldo’s flex technology, which promises extra bendability and comfort so you can wear them all daylong.

Aldo, aldoshoes.com | $220

Aigle 'Aiglentine' rainboots, $265 at Gravity Pope, gravitypope.com.

SPLISH SPLASH

For boots that do double duty — look stylish and actually protect you from the elements — look no further than Aigle’s “Aiglentine” rain boot. Handmade in France, they’re an investment compared to other wellies out there but they’re definitely one of the most stylish, feminine pairs of waterproof shoes we’ve ever seen. Contoured, with an adjustable calf strap, they have an equestrian-inspired cut and details, as well as a cushioned insole and tread sole that’s ideal for our wet weather.

Gravity Pope, gravitypope.com | $265

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