The Easy Way to Style Over-the-Knee Boots

“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.

how-to-wear-over-the-knee-boots-now-242271-1510787780921-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787783584-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787786247-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787788510-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787792392-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787795982-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787798476-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787800797-image

(Image credit: Getty Images)

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

how-to-wear-over-the-knee-boots-now-242271-1510787803318-image

(Image credit: Getty Images)

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

how-to-wear-over-the-knee-boots-now-242271-1510787805845-image

(Image credit: Getty Images)

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

how-to-wear-over-the-knee-boots-now-242271-1510787809365-image

(Image credit: Getty Images)

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

how-to-wear-over-the-knee-boots-now-242271-1510787811678-image

(Image credit: Getty Images)

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

how-to-wear-over-the-knee-boots-now-242271-1510787814061-image

(Image credit: Getty Images)

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

how-to-wear-over-the-knee-boots-now-242271-1510787816153-image

(Image credit: Getty Images)

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

how-to-wear-over-the-knee-boots-now-242271-1510787819016-image

(Image credit: Getty Images)

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

how-to-wear-over-the-knee-boots-now-242271-1510787821295-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787824889-image

(Image credit: Collage Vintage)

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

how-to-wear-over-the-knee-boots-now-242271-1510787828111-image

(Image credit: Collage Vintage)

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.

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including Vogue.com, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.