The Easy Way to Style Over-the-Knee Boots

by Kristen Nichols

“I can’t pull off over-the-knee boots,” a friend recently told me. “They just don’t work for me.” It’s something I hear every time winter rolls around, followed by gripes about how tricky the thigh-high style is to pull off. But here’s where I disagree. I think anyone can wear the winter boot staple: It just really comes down to making them work with your personal style. That could mean pairing them with a miniskirt and a hoodie, wearing them with a wrap dress with exaggerated sleeves, or even layering them under a cool statement coat.

Ahead, get ideas for how to wear over-the-knee boots with 18 cool outfit ideas.

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Update your all-black outfit by adding an oversize coat and over-the-knee boots. 

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Create a cool, put-together look by pairing a statement top and a long coat with your simple boots. 

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Floor-length coats are everywhere this season. Style yours with a simple belted dress and boots. 

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Make a statement with a mixed-pattern dress and eye-catching red boots. 

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Show off the color of the season by copping a pair of red over-the-knee boots and pairing them with an oversize jacket. 

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A cool patterned dress–and-turtleneck duo looks great with simple black boots. 

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Try out a pair of bold over-the-knee boots with a sleek skirt-and-sweatshirt combo. 

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Statement shoulders continue to be a thing—add a pair of over-the-knee boots and leggings for a seriously edgy vibe.

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Transform your look from day to night by pairing a sheer dress with slouchy statement boots. 

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A sophisticated and color-coordinated skirt and blouse look so cool with over-the-knee boots.

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Create a chic office look and style a tailored blazer with your over-the-knee boots. 

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Try out a graphic tee tucked into a sleek leather skirt for a tried-and-true cool-girl look. 

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Accentuate your figure by belting a long patterned coat at the waist and adding statement boots. 

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Stay warm by belting a puffy oversize jacket to make a chic dress. 

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For a cool unexpected look, style your over-the-knee boots with an oversize sweatshirt and coat. 

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Create the coolest Buckingham Palace–ready look by pairing a checked sweaterdress with a chic fiddler hat. 

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Stay cozy with a long fur coat and brown boots with warm fall colors. 

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Try out a pair of detailed over-the-knee boots, and wear them with an all-black ensemble and an oversize fur coat.

Next, read about the new way to wear winter dresses.

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