Fashion People Agree—This Is the One Boots Trend That Comes Back Into Style Every Single Year

I consider myself an anti-trend shopper. Whilst I work in the fashion industry and keep my finger on the pulse of new season trends, I always consider the longevity, and whether it can serve me for more than a couple of seasons before I commit it to my wardrobe. Whilst I've been temped by some of the new boot silhouettes taking over my timeless this season, my heart of hearts knows that it's classic riding boots that will always pull their weight in a capsule wardrobe.

Influencer wears riding boots.

(Image credit: @_livmadeline)

Void of excess embellishment, riding boots extend up to the knee and feature a simple rounded toe and polished leather exterior. Designed with a small heel, these boots were—as the name suggests—originally designed for use by equestrians and are crafted so as to be able to hook around a stirrup, making practical and comfortable, and ideal of daily wear.

Long adopted by the style set, this timeless shoe trend reemerges every winter in style crowds, often styled with a mini skirts and midi skirts, or worn tucked in to leggings and slim-fitting trousers—as initially designed to do.

Influencer wears riding boots.

(Image credit: @emmanuellek_)

Rather than cowboy boots and biker boots that seem to distinctly ebb in and out of favour with the years, this enduring favourite utilises a low-key design that makes it an outfit chameleon—styling well with just about everything. A winter wear no-brainer, style with a dress and tights whilst we wait out the rest of autumn, before pairing with fleece-lined leggings or slim-fitting jeans come winter.

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(Image credit: @fakerstrom)

Read on to shop our edit of the best riding boots to buy now.

SHOP OUR EDIT OF THE BEST RIDING BOOTS:

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Senior Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.