How To Wear Over-the-Knee Boots

The key to wearing very tall over-the-knee or thigh-high boots is balance. For example, if you want to rock them over your jeans, wear a pair that are ultra-skinny, have lots of stretch and fit much like leggings. You also want to make sure they are only as long as your ankle, to avoid bunching.

Over-the-knee or OTK boots are a bold look, so if you want to tone it down a bit but still wear, say, a skirt or tight dress, you can use layers to keep things casual. An on-trend long wrap coat works well, as does a fun faux fur.

Either way, we recommend wearing knee-high or boot socks with your over-the-knee boots, and putting them on before your jeans, so they lay smooth over your shins and calves. (Just a helpful little trick from us to you. And while black is the most popular color for this style of boots, don't be afraid to try a different hue, like grey or sandy beige.

Below, see five of our favorite ways to rock OTK or thigh-high boots, inspired by celebrities and street style during Fashion Week.

of 05

With a Mini Skirt and Sweater

The key to pulling off over-the-knee or thigh-high boots with a mini skirt is to layer a bit and always think about proportion. If your skirt is tight, try wearing it with a cozy, oversize sweater. Adding a coat also makes your tall boots more casual for daytime.

Get the look with these Ivanka Trump boots.

of 05

In a Monochromatic Look

Break up an all-black look by mixing textures. With an oversized furry coat and legging-style jeans, you can rock ultra-sexy thigh-high boots with a killer heel and not feel like Julia Roberts in Pretty Woman. (If you catch our drift.)

Get the look with these Steve Madden boots.

of 05

With Contrasting Denim Leggings

In order to wear jeans tucked into your boots, you'll need your tights, most legging-like pair to avoid bunching. We love the look of pairing black jeans with charcoal or grey jeans to provide a little contrast, and really let your boots stand out.

Get the look with these Stuart Weitzman boots.

of 05

With a Dressy Blazer

Kendall Jenner's Balmain x H&M look may seem intimidating, but hear us out. You can layer a camisole under your blazer and add thick tights or leggings under your boots for a deceptively sleek appearance. Just be sure your blazer has pretty details like beading or velvet to make your look cocktail party-ready.

Get the look with these Stuart Weitzman boots.

of 05

With a Short Dress and Long Coat

Street Style - Day 2 - New York Fashion Week: Women's Fall/Winter 2016 — Georgie Wileman / Getty Images

We love the proportion play of wearing a short dress and tall boots with a jacket that covers a little bit of both. The look is fun and sophisticated—plus it will keep you warm in winter and early spring.

Get the look with these Steve Madden boots.

How To Wear Over-the-Knee Boots