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.

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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.

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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.

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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.

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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.

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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.