How to Wear Winter Boots with Jeans

Co-authored by Dina Scherer and Hannah Madden

Last Updated: October 26, 2021 References

Wearing boots is the perfect way to keep your feet warm in the winter while staying fashionable. With so many different styles of boots and jeans out there, it can be hard to figure out what pairs well with what. Fortunately, if you keep a few guidelines in mind, you can pick out outfits that are stylish and cool to rock your winter wardrobe this season.

1

Tuck skinny jeans into snow boots for an easy look.

Skinny jeans won’t bunch up around your ankles, so they’re the best choice.^{[1]
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Dina Scherer
Wardrobe Stylist & Personal Shopper
Expert Interview. 22 October 2021.} Pull on your favorite pair of skinny jeans, then add a pair of lace-up boots, snow boots, or duck boots to finish off your outfit.^{[2]
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- If you want to stay extra cozy, put on a pair of fluffy socks and let them peek out the top of your boots.
- Tucking jeans into boots looks best when your jeans and your boots are the same color.
- If you’d like to look taller, choose booties with a slight heel.

2

Pair cropped jeans with ankle boots to show some skin.

You don’t have to cover up completely in the winter. Put on a pair of cropped jeans, then add a pair of ankle boots to leave around 1 in (2.5 cm) of your skin showing.^{[3]
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Dina Scherer
Wardrobe Stylist & Personal Shopper
Expert Interview. 22 October 2021.}
- Try wearing black jeans with black boots, then pairing them with a black shirt for a monochromatic outfit.
- Or, stay classic with blue jeans, a white shirt, and brown boots.

3

Try flare jeans with high-heel boots.

Your boots don’t have to be the star of the show. Pull on a pair of flared jeans, then wear a sock boot or a high-heeled bootie that’s tight around your ankle.^{[5]
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- The tighter the boot fits around your ankle, the better. If the fit is too wide, your jeans could get caught in the top of the boot, leading to bunching and scrunching.
- Black boots look great with dark wash denim, while brown boots look good with light wash jeans.

4

Try relaxed fit jeans with snow boots for a contemporary outfit.

Keep your feet warm in this cool and casual look. Put on a pair of relaxed fit or straight-legged jeans, then pull your duck boots or snow boots on. Let your jeans flare out over the boots as you hit the town.^{[6]
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- You can pair this outfit with a long coat and a fluffy hat to stay warm.

5

Stack boot cut jeans on your boots for a more relaxed feel.

Looking casual isn’t hard with a pair of jeans and some boots. Put your jeans on, then slide your boots on after them. Pull your jeans up over the boots so they stack on top in a scrunched pile.^{[7]
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Dina Scherer
Wardrobe Stylist & Personal Shopper
Expert Interview. 22 October 2021.}
- This trick works best with skinny or relaxed fit jeans. Boot cuts and flares won’t stay scrunched very well.
- This is one of the easiest ways to pair boots with jeans, and it requires almost no effort!

6

Roll your jeans up to keep them outside your boots.

Longer jeans can be hard to style with ankle boots. Put your boots and your jeans on, then roll your jeans up twice to expose the lighter inside color of the denim.^{[9]
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- The contrast between the inside denim color and the outside denim color will draw attention to your boots.
- This look works great with ankle booties or lace-up boots.

7

Cuff your jeans for a hip, modern look.

A large cuff will draw more attention to your boots. Put your jeans and your boots on, then roll your jeans up once so they sit on top of your boots.^{[10]
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Dina Scherer
Wardrobe Stylist & Personal Shopper
Expert Interview. 22 October 2021.}
- Large cuffs like this can make you look a little shorter. If you’re going for the illusion of length, stick to rolling your jeans up instead.
- Large cuffs look great on dark wash jeans with brown boots.

8

Go monochromatic with an all-black outfit.

When you’re not sure what to wear, this is the perfect look to pick. Pair black boots, black jeans, and a black top for an effortlessly stylish outfit.^{[12]
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- If you want to add a pop of color, throw on a bright jacket or scarf as a nice contrast.
- Make sure all your blacks are the same shade and tone for a seamless outfit.

9

Keep it classic with dark denim and brown boots.

You can’t go wrong with a simple look. Put on some dark wash jeans, brown boots, and a white T-shirt for some all-American style.^{[13]
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- Throw on a flannel if you’re feeling chilly, or grab a puffy jacket to stay extra warm.^{[14]
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  Dina Scherer
  Wardrobe Stylist & Personal Shopper
  Expert Interview. 22 October 2021.}

10

Match your boots with a blazer for a business casual outfit.

You can take your boots to the office by getting a little dressed up. Put on a pair of dark wash jeans and some boots, then match the color of your boots with a plaid blazer.^{[15]
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Dina Scherer
Wardrobe Stylist & Personal Shopper
Expert Interview. 22 October 2021.}
- Put on a polo shirt underneath your blazer for extra professionalism.
- If it’s super cold outside, wind a small scarf around your neck to stay warm.

Expert Q&A

Question

How do you wear winter boots with straight leg 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

Taller boots tucked in usually look more flattering when combined with skinny or straight leg jeans. If the boots are shorter in the ankle, you can let the jeans sit over them. You can also cut them to expose a bit of skin!
Question

How do you wear jeans with boots?

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

That's a great combination of styles that usually blend well with a lot of different outfits. You can combine them with a T-shirt, a sweater or a blouse, preferably tucked in to create more emphasis on your waist.