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How to Wear Over-the-Knee Boots: A Street-Style Guide

As the weather starts to chill, we see stylish ladies in the world’s fashion hubs boot up. Although ankle-grazing booties are still popular, many fashion fans are taking their footwear to dramatic heights with thigh-high, over-the-knee boots.

Wearing an OTK (that’s industry shorthand) can initially seem daunting. Their sexy thigh-circling style might feel like too much for daywear or, for many, too much for any hour. Non-leggy ladies may also fear that their height will cause less-than-supermodel-length stems to seem squat. These are valid concerns, but we have a couple of tips to allay them.

How to Wear Over-the-Knee boots

Sofie Valkiers and Evangelie Smyrniotaki at Paris Fashion Week

A simple mini sheath dress is the easiest article of clothing to pair with extra-tall boots. These dresses keep things neat and short, allowing the boots to stand out, which they’ll do no matter what you wear. But by not overwhelming your look with too many layers or accessories, the boots act as an essential part of, rather than an excessive addition to, the outfit. Petite ladies will have the best success with this dress and boot combo.

Veronika Heilbrunner at Fashion Week A couple of fit tips:

  • Either allow for about three inches of space between your boot top and dress hem—like Sofie above left—or wear a very fitted boot, one in an almost socklike stretch material, that covers the entire leg—like Evangelie above right.
  • A sheath dress, or another loose silhouette, looks more elegant with an OTK than a tighter-fitting frock. Because the thigh-high height draws attention to the legs, it’s best to let the eye linger there rather than trying to compete with body-con numbers.





Veronika Heilbrunner 

Chiara Ferragni and Doina Ciobanu at Fashion Week

Chiara Ferragni and Doina Ciobanu
Shea Marie and Caroline Vreeland at Fashion Week

Another trending way to wear the over-the-knee boot is with a hoodie. Yes, just a sweatshirt. Shocking as it may sound, you don’t necessarily have to go sans pants—although some ladies wear it that way. The lengthy boot provides a little coverage, but a teeny skirt (as Chiara did above left) or pair of short-shorts underneath the oversized shirt will keep things less breezy below. The OTK boot dresses up this casual top while leaving it relaxed enough for the day but translatable to evening drinks.

A couple of fit tips:

  • Taller ladies may want to opt for a flatter-heeled boot with this look. More petite ladies will still benefit from a heel here, but may not want to wear a stiletto or something quite sky-high with just a hoodie.
  • A solid-colored sweatshirt will look longer and more like a dress than something too patterned or graphic.

Shea Marie and Caroline Vreeland at Milan Fashion Week

Serena Williams and Martha Graeff

Serena Williams and Martha Graeff

Wearing this boot with pants quickly updates your basics. The OTK looks great with jeans and a blouse or a sweater and leggings. Naturally, finding the boot with the right shaft width and height is key (our site allows you to shop by these measurements). Also, you’ll want to pair it with pants that don’t have a lot of excess fabric or much bagginess. A skinny or stretch pant is the most accommodating.

A couple of fit tips:

  • Match your pant and boot color to create a longer leg line. A high-waist pant with a tucked-in shirt also helps lengthen the leg.
  • The boots are a layer. Don’t overwhelm your outfit by piling on too much. Keep the palette of your outfit’s bottom half to two colors at most.

Fil Xiaobai and Kristina Bazan

Fil Xiaobai and Kristina Bazan

These tiny style dynamos show that the over-the-knee boot isn’t just for giantesses. Worn with a mini and some hosiery, the boot suits any size. Notice how both Fil and Kristina keep their colorways minimal—to two shades exactly. A high heel and showing a little thigh between the boot top and skirt hem glamorously accentuates their gams. Try not to show much more skin than that bit of leg to keep things elegant, but still sassy.

A couple of fit tips:

  • A cropped jacket or a tucked-in shirt helps make the legs seem longer.
  • A boot style that cinches around the thigh will make shorter ladies look like they’re wearing the boot, not sinking into it.

Valentina Ferragni and Nina Schwchtenberg

Valentina Ferragni and Nina Schwichtenberg

With bare legs, the over-the-knee boot looks great with a short skirt—even shorts—cloaked by a long jacket. This style is great for fall, as it allows for you to bare a little skin while staying wrapped up. Choose a jacket that drapes well so that, like Valentina and Nina, you can casually throw it over your shoulders for quick commutes. You’ll see a lot of black OTKs this season, but these taupe and grey shades are a nice neutral that can be worn with most anything.

A couple of fit tips:

  • A neutral tone, like beige, taupe or grey, looks great with a bare leg while still seasonal.
  • Keep a fall or winter coat open to show off your style. Choose a coat style with some volume so that it drapes and moves well.

SHOP: over-the-knee boots

—Britt Olson