How To Wear An Over-The-Knee Boot Like A Street Style Star

Sandals are the shoe of summer, but come fall things get a little more complicated. There are classic ankle boots, sleek loafers, girly Mary Janes, and the most eye-catching of them all: over-the-knee boots, which were a favorite silhouette among the Fall/Winter 2020 collections. "Believe it or not, there is practicality here," Chloe King, digital fashion lead at Bergdorf Goodman, tells TZR about the emerging trend. After all, she notes, the shoe keeps you much warmer than a pair of tights.

"With Fall/Winter 2020 favoring some super-short hemlines via micro shorts and miniskirts, over-the-knee boots are the weather-friendly workaround for these shrunken lengths," Celenie Laura Fleur Seidel, senior womenswear editor at Farfetch, tells TZR. As the shoe works equally well under both a side split skirt or a dramatic sweeping coat, Seidel says the bold silhouette can work for anyone. "From Ann Demeulemeester’s sleek and ultra-practical combat iteration to heeled, seductive second-skin versions from the likes of Alexander McQueen, Bottega Veneta, Proenza Schouler, and Saint Laurent, Fall/Winter 2020 saw this trend spanning all aesthetics from the most minimal and utilitarian, to high glam."

Proenza Schouler Fall/Winter 2020. Photo: Gotham/GC Images

As for wearing the shoe IRL, the street style outside Spring/Summer 2021 shows this past September proved it's not as intimidating of a trend as you might make it out to be. You can wear the tall boots with an ultra-glitzy dress or tuck your favorite trousers into them. Plus, as King notes, when worn with a long sweater or jacket, an over-the-knee boot replaces the need for pants altogether.

Experts agree, it's worth it to dedicate a (substantial) section in your boot storage to a pair of over-the-knee boots this season. Below, find 10 ways street style stars are wearing the style.

We only include products that have been independently selected by The Zoe Report's editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

How To Wear The Over-The-Knee Boot Trend: Just A Touch Of Color

Pierre Suu/Getty Images

Update a polished long coat and black trouser outfit with a pop of color via your over-the-knee boots and a coordinated bag. The accessories will add just the right punch to a minimalist look.

How To Wear The Over-The-Knee Boot Trend: Tone Down Prints

Christian Vierig/Getty Images

A black leather boot is arguably the most versatile style you can own. Wear an over-the-knee style with anything from a simple neutral ensemble to a colorful matching set.

How To Wear The Over-The-Knee Boot Trend: Go Trendy

Darrel Hunter

If your style is trend driven, opt for a sleek snakeskin boots. Match the shoe with coordinating brown separates and you'll look put together, but not overly so. Add a pop of color via a handbag (and mask!) and you're set.

How To Wear The Over-The-Knee Boot Trend: Grungy Chic

Darrel Hunter

A chunky sole is both durable and on-trend for this season. If you're worried about coming off as too edgy, style the shoe with a playful print or bright color.

How To Wear The Over-The-Knee Boot Trend: Elevated Dress

Pierre Suu/Getty Images

Since ribbed knits are a must-try in 2020, test out a cozy ribbed dress with an over-the-knee boot. If you're looking for a style that's a bit more polished, opt for a puff-sleeve slit dress.

How To Wear The Over-The-Knee Boot Trend: High Slits

Christian Vierig/Getty Images

Like Seidel mentions, an over-the-knee style works well styled under a slit skirt since you can see it in full. Try an all-black or gray ensemble to keep things cohesive.

How To Wear The Over-The-Knee Boot Trend: Summer Meets Fall

Jeremy Moeller/Getty Images

Eager to wear shorts in the fall? Simply couple the bottoms with an over-the-knee boot to keep warm. Complete the look with a matching leather shirt jacket, and add tights as the weather continues to chill.

How To Wear The Over-The-Knee Boot Trend: Modern Color Schemes

Christian Vierig/Getty Images

Navy blue and white are a go-to summer color combo. But for a fall take on the color scheme, try the tones out by styling a navy blazer with white leather boots.

How To Wear The Over-The-Knee Boot Trend: Dress It Up

Edward Berthelot/Getty Images

White ankle boots are a staple come fall, but this time around opt for an over-the-knee iteration. Dress them up with a glitzy dress or try skinny jeans and a checkered jacket for something more everyday.

How To Wear The Over-The-Knee Boot Trend: Play On Textures

Gotham/GC Images

Though not pictured at fashion week, Kourtney Kardashian's over-the-knee boot ensemble is a further indication that the boot is on the rise. Try a play on textures like Kardashian with a leather trench and suede boot.