12 Sleek Riding Boots Even Princess Diana Would Wear

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Princess Diana undoubtedly left behind a legacy of goodwill and sartorial prowess. From her checkerboard trousers to casual sweater and biker short combinations, her apparel choices have continued to inspire fashionistas for decades. That’s not to say her shoes weren’t equally as notable, though. Alongside chunky sneakers and sensible loafers (both of which have been trending for at least a few seasons), the late Lady Di also had a penchant for riding boots.

Often characterized by its tall shaft and low heel design, the classic silhouette has withstood the test of time. Since debuting in the 10th century as a shoe built for horseback riding, it’s become a modern staple among everyday shoppers and celebrities. The equestrian look has appeared all over runways. Most recently, it pervaded fall ’20 collections, with designers at Dior, Valentino and Michael Kors offering up no-frills versions perfect for rounding out a capsule wardrobe.

While the styling options are endless, we suggest following Diana’s lead and wearing them over tight jeans (Kate Middleton is a fan of this pairing, too). You can also sport them with joggers and a belted coat, an outfit that can comfortably be worn from your at-home office setup to the local grocery store.

Princess Diana riding boots

For those on a budget, mass market brands also offer their own wallet-friendly takes on the boot. Some options even feature subtle hardware and strappy embellishments if you prefer a slightly dressier look.

Ahead, we rounded up 12 of our favorite riding boots we’re sure Princess Diana would wear today. While not all these styles are actually suited for an afternoon at the stables, they’re bound to be heavy in your street style rotation.

Sam Edelman Penny Leather Riding Boot

A burnished toe design and elegant snap detailing along the shaft make this pair an elevated staple. For easy on and off access, the popular silhouette also features a side zipper at the back for easy on and off access.

CREDIT: Courtesy of Zappos

Tory Burch Brooke Knee Boot

This classic black boot from Tory Burch features a touch of hardware and low one-inch heel for a minimal boost of height.

CREDIT: Courtesy of Tory Burch

Vince Camuto Prolanda Knee High Boot

Varied textures always add intrigue to a pair of shoes or piece of clothing. We love that this statement boot features a paneled leather and textile upper, plus elegant chain-link accents.

CREDIT: Courtesy of Nordstrom

Tommy Hilfiger Deelia Boot

You can never go wrong with a no-frills style like the Delia boot, complete with a stacked heel, subtle logo design and elastic panel at the back for comfort.

CREDIT: Courtesy of DSW

Karen Scott Vickyy Riding Boots

Another cool textured boot, this model features a manmade upper with a croc-embossed cuff. It’s also a great option for people with wide calves, since it includes a larger 17.5-inch opening at the shaft.

CREDIT: Courtesy of Macy's

Clarks Orinoco 2 Waterproof Riding Boot

Just as functional as it is stylish, this sophisticated Clarks boot features Gore-Tex waterproofing and insulation to keep feet dry and warm in wet weather. It also boasts an inner side zipper so you can easily pull these off your feet at the end of a long day.

CREDIT: Courtesy of Nordstrom

Naturalizer Jackie

Not only will this buckled silhouette pair nicely with all your off-duty outfits, it also offers the brand’s dual density cushioning and arch support to keep you comfortable.

CREDIT: Courtesy of Zappos

Ariat Carden Waterproof Boot

Complete with detailed hardware and styling inspired by Jodhpurs (or English riding pants), this nubuck leather pair offers a truly authentic look. And according to the brand’s website, the rugged style looks even better the more you wear it. The silhouette is also waterproof and features the brand’s ATS technology for stability and comfort.

CREDIT: Courtesy of Ariat

Coach Itona Riding Boot

Snakeskin subtly makes its way into this modern leather style, appearing on the harness and shaft straps for a nice contrast.

CREDIT: Courtesy of DSW

Bed Stu Manchester

Reminiscent of popular corset and bustier trends, these boots feature an intricate lace-up design at the back of the shaft. Their distressed leather upper and contrast stitching add rugged appeal.


CREDIT: Courtesy of Zappos

Frye Melissa Button 2

Frye does its equestrian-inspired boot with a durable Italian leather upper, asymmetrical topline and signature button accents. It should be comfortable to wear for whatever activities the day brings you, as it features a cushioned insole and rubber heel insert for added traction.

CREDIT: Courtesy of Zappos

Cole Haan Grand Ambition Huntington Boot

The ultimate work and party boot, this sleek design boasts versatility and technical prowess. Designed in partnership with University of Massachusetts Amherst’s Biomechanics Laboratory, the pair is made to offer an ultra-flexible and supportive fit, featuring a stretch back panel and contoured footbed with Cole Haan’s signature Grandføam cushioning.

CREDIT: Courtesy of Cole Haan

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