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How To Wear Over The Knee Boots This Winter In 7 Cool (But Also Warm) Ways

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When you're building a winter footwear wardrobe, it's important to ask the right questions — can sneakers survive snow? How many pairs of boots are too many, really? More than anything else in your closet, shoes have to be able to weather the elements; snow, sleet or otherwise. But, just because your shoes have to be practical, doesn't mean they can't be cute, which is exactly why you need to invest in a pair of tall boots this season. While figuring out how to wear over-the-knee boots may seem intimidating at first (they cover a lot of leg after all), the reality is that they're surprisingly versatile, not to mention the fact that they keep your legs plenty warm.

The most notable example of knee-high boots from the SS19 season was at Jeremy Scott, who designed shoes in his signature neon, club-kid style. But, knowing such high-saturation footwear isn't for everyone, there are plenty of more classic options in leather, suede, and even snakeskin worth giving a go.

The ultimate key to styling these boots is to find the right proportions. For some that might mean a short hemline with a tall boot, and for others that might mean a chiffon midi skirt with a knee-high style. Whatever your personal style, there is a tall boot out there for you this winter and the outfit inspiration you've been searching for is all below.

Pair Them With A Midi Dress

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Don't fret if your hemline lands below the top of your boots. An asymmetrical cut means you can still see a flash of your over-the-knee boots. To maximize coverage in the cold, layer a camel coat or wool blazer on top of the printed dress.

Leopard-Print Chiffon Midi Dress

$1,715

Petar Petrov

Hiline Over-The-Knee Boots

$1,024

Stuart Weitzman

Oversized Sunglasses

$272

Givenchy

Play With Mixed Textures

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If you want to stay within the same color family, vary the textures of each piece you choose to add a bit of extra visual interest. Try boots in a soft suede and contrast them with rich velvet, leather, or a chunky knit.

Rubina Wool Coat

$695

Soia & Kyo

Farrow Crop High Rise

$199

DL1961

Casper Boots

$595

Vince

Stand Out With A Fun Pattern

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Find a patterned skirt to pair with over-the-knee boots to add a playful edge to sleeker footwear styles. Keep the rest of the outfit simple to let the pairing shine.

Acacia Jacket

$1,595

Altuzarra

Asymmetric Tartan Cotton Mini Skirt

$455

Vivienne Westwood

Rodeo Boot

$298

Raye

Dive Into Monochrome

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A pair of over-the-knee boots in an emerald green would pair well with grey sweaters, black coats, and any white knitwear. But to break from subdued winter dressing, go for something a bit more colorful. A rich jewel-tone shade won't let you down.

New Divide Coat

$796

Theory

Sunburst Pleated Midi Skirt

$99

Eloquii

Pointed Knee-Length Boots

$386

Paris Texas

Match Bold Boots With An Equally Bold Coat

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You can create a unique silhouette by pairing a slightly cropped jacket in a bright color on top of a pair of boots that come up far over your knee. The result is a cool girl outfit that will have people doing double-takes trying to determine whether you're wearing pants or boots.

Pixie Coat

$86

I AM GIA

Equipe Hoodie

$195

Fiorucci

Plaid Over-The-Knee Boots

$1,309

Off-White

Get Inspired By a Statement Piece

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One easy way to wear more color is to select a bold statement coat and then add in accessories that coordinate. Red over-the-knee boots, denim skirt, and black bag all refer back to a multi-color topper like the one above and pull the look together.

Long Knitted Cardi-Coat

$2,328

Missoni

Grlfrnd x Revolve Milla Denim Mini Skirt

$158

Grlfrnd

Ashlina Over The Knee Boots

$200

Vince Camuto

Fall In Love With Neutrals

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If creams and browns are the way to your heart, know that you can still stand out when sticking to neutrals. A shearling or teddy long coat in white paired with tall snakeskin boots may feel like a lot, but the toned-down color palette makes it wearable for everyday.

Faux Shearling Coat

$179

& Other Stories

Heeled Snakeskin Print Boots

$100

Zara

Stella Satchel

$328

Rebecca Minkoff