What Can You Wear with Over-the-Knee Boots? 10 Trendy Outfits

Co-authored by Dina Scherer and Hannah Madden

Last Updated: December 14, 2021 References

Over the knee boots are the perfect footwear for the fall, winter, and spring. If you have a pair that you just can’t wait to wear out, look no further! We’ve compiled all the clothes you can wear with your boots to look fabulous every time you step out the door.

1

Show off your legs in a mini skirt.

Get dressed up to go out and show off some skin. Pair your over the knee boots with a mini skirt that hits about mid-thigh.^{[1]
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Dina Scherer
Wardrobe Stylist & Personal Shopper
Expert Interview. 24 August 2021.} Then, throw on a T-shirt or a tank top to complete your look. Accessorize with some dangly earrings and a few flashy rings to look cool and confident.^{[2]
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- Mini skirts are great for going out, but not so great for the office. Save this look for when you’re heading out on the town with friends.
- Wear this look with your favorite heeled over the knee boots to elongate your legs.^{[3]
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  Dina Scherer
  Wardrobe Stylist & Personal Shopper
  Expert Interview. 24 August 2021.}

2

Wear skinny jeans for a casual, everyday look.

Jeans tucked into boots can be paired with almost anything.^{[4]
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Dina Scherer
Wardrobe Stylist & Personal Shopper
Expert Interview. 24 August 2021.} If you have brown or gray boots, try pairing them with light wash skinny jeans. If your boots are a darker color, go with dark wash skinny jeans. Pair your look with a flowy blouse or a button-down to look chic yet casual.^{[5]
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- Stay away from boot cut or flare jeans, since those tend to bunch up inside of boots.
- This look works for both heeled boots and flat ones.
- Accessories with your favorite handbag and some simple stud earrings.

3

Stay cozy in a sweater dress.

In the winter, stay cozy with your favorite dress and boots. Throw a sweater dress on that hits just above your knees, then pair it with your over the knee boots. If you’re dressing up, wear your heeled boots; if you’re staying casual, wear your flat ones. Add a statement necklace and a few bangles before you head out the door.^{[6]
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- Try contrasting the color of your dress with the color of your boots. For instance, if your boots are brown, go for a gray or bright-colored dress.
- If your boots are black, try a light-colored neutral, like white, cream, or tan.
- This is a good outfit to wear to work during the winter time.

4

Tuck leggings into your boots for a sporty look.

Embrace athleisure wear with this outfit. Grab your black leggings and tuck them into your boots, then pair your outfit with a tanktop and a wind breaker. Throw your essentials into a backpack or a fanny pack to keep them on you.^{[7]
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- This outfit works best with black boots, since they’ll blend into the leggings and create a seamless transition.

5

Try a midi skirt for a chic outfit.

Look modern and stylish for a night out. If you don’t want to show much skin, pair your boots with a midi skirt that hits just below your knees. Add a fitted crop top to balance out your silhouette, and pair your outfit with a structured handbag.^{[8]
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- Try to contrast the color of your boots with the color of your skirt. That way, you’ll be able to see the boots peeking out from underneath the fabric of your skirt.

6

Wear sheer, black tights if it’s cold out.

Black tights always look good with over the knee boots.^{[9]
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Dina Scherer
Wardrobe Stylist & Personal Shopper
Expert Interview. 24 August 2021.} If it’s cold out, cover up your exposed skin. Throw on a pair of sheer, black tights to keep your legs covered while you wear a skirt. If you have brown boots, try wearing gray or patterned tights to mix it up.^{[10]
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- Tights are a great addition to any outfit with a mini skirt.

7

Try an oversized blazer for a streetwear look.

A chunky blazer can elevate your look to a high fashion outfit. Throw on a fitted mini skirt and your over the knee boots, then pair it with an oversized blazer that matches your skirt. Accessorize with a few thin necklaces and some rings to look cool and put-together.^{[11]
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- Gray, brown, and black blazers look good with almost any color of boots.
- If you want to really embrace the faux-professional look, wear a tie underneath your blazer.

8

Dress up in a maxi dress.

Try one with a slit in the front to showcase your boots. Throw on a maxi dress that has a slit or buttons down it, like a shirt dress. Throw on your over the knee boots to complement the long silhouette of your dress.^{[12]
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- If you really want your boots to stand out, pick a neutral-colored dress, like black or white.
- Accessorize with a few bangles and some simple stud earrings.

9

Throw on an overcoat for a modern outfit.

Overcoats mimic the long, lean lines of over the knee boots. If you’re ever chilly in any of your outfits, grab a long overcoat or peacoat that hits below your knees. The color doesn’t have to match your boots, but it should look cohesive with the rest of your outfit.^{[13]
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- For instance, a gray peacoat would work well with black or gray boots.
- A brown overcoat would look nice with brown or gray boots.

10

Try an oversized tee for a punk rock fit.

Get a little edgy with a look that stands out. Throw on a large T-shirt that hits about mid-thigh, then pull on your over the knee boots. This look works best with heeled boots to elongate your legs and add a bit of extra edge to your outfit.^{[14]
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- If you don’t want to wear just a T-shirt, try adding a pair of biker shorts underneath.
- Or, throw on a pair of sheer black tights to cover your legs.

Expert Q&A

Question

Can you wear over-the-knee boots with jeans?

Dina Scherer
Wardrobe Stylist & Personal Shopper
Dina Scherer is an Image and Wardrobe Stylist and the Founder of Modnitsa Styling, based in New York City. With over a decade of experience, Dina specializes in color analysis, style development, closet editing, and personal shopping. She helps her clients elevate their personal style and curate a wardrobe aligned with their lifestyle. Dina holds degrees in Advertising and Marketing, Fashion Merchandising, and a Certificate in Image Consulting from the Fashion Institute of Technology.

Dina Scherer

Wardrobe Stylist & Personal Shopper

Expert Answer

Oh, for sure! Try pairing jeans and a cardigan sweater, tucking a little t-shirt underneath it. Have the boots over your jeans to really show the full look, without hiding the boots.
Question

Is it OK to wear knee-high boots in spring?

Dina Scherer
Wardrobe Stylist & Personal Shopper
Dina Scherer is an Image and Wardrobe Stylist and the Founder of Modnitsa Styling, based in New York City. With over a decade of experience, Dina specializes in color analysis, style development, closet editing, and personal shopping. She helps her clients elevate their personal style and curate a wardrobe aligned with their lifestyle. Dina holds degrees in Advertising and Marketing, Fashion Merchandising, and a Certificate in Image Consulting from the Fashion Institute of Technology.

Dina Scherer

Wardrobe Stylist & Personal Shopper

Expert Answer

Definitely. Wear a skirt or dress with stockings and the over-the-knee boots on top of the stockings. Bonus points if you can match your stockings to your boots.
Question

Do over-the-knee boots make your legs look longer?

Dina Scherer
Wardrobe Stylist & Personal Shopper
Dina Scherer is an Image and Wardrobe Stylist and the Founder of Modnitsa Styling, based in New York City. With over a decade of experience, Dina specializes in color analysis, style development, closet editing, and personal shopping. She helps her clients elevate their personal style and curate a wardrobe aligned with their lifestyle. Dina holds degrees in Advertising and Marketing, Fashion Merchandising, and a Certificate in Image Consulting from the Fashion Institute of Technology.

Dina Scherer

Wardrobe Stylist & Personal Shopper

Expert Answer

In some cases, yeah. If paired with matching stockings, you can create a longer leg line so it doesn't feel like you're breaking up your leg in different parts with horizontal lines and different colors.