9 Knee-High Boots Outfits to Upgrade Your Winter Style

The ultimate way to get through this season.

knee high boots outfits

Design by Tiana Crispino

Knee-high boots are as stylish as they are practical. Depending on your style, the statement shoes can be paired with dresses or denim looks. Due to their comfort and durability, they're a great option for a winter shoe. They transform seamlessly from day to night and can be elevated or casual, depending on the rest of your outfit.

Whether you're looking for a flat shoe or a three-inch heel, we've got you covered. From delicate maxi dresses to oversized biker jackets, keep scrolling for nine different ways you can style knee-high boots outfits.

With Leggings and a Sweatshirt

outfit 1

Design by Tiana Crispino

Athleisure meets street style when you pair knee-high boots with leggings and a cozy oversized sweatshirt. Add hoop earrings and you have a comfortable yet elevated everyday look.

With a Floral Maxi

outfit 2

Design by Tiana Crispino

Think Little House on the Prairie and western chic when you pair together this groovy maxi dress and suede knee-high boots. The suede saddle bag brings out the earthy tones in the dress.

With a Blazer and Jeans

outfit 3

Design by Tiana Crispino

Dress to impress with these classic yet statement-making boots from Stuart Weitzman. Style with tight denim and an oversized blazer (unbuttoned) for an easy, sensual look.

With a Sweater Dress

outfit 4

Design by Tiana Crispino

Grab your favorite cozy knit dress and pair it with slouchy, heeled knee-high boots for a night out with friends. Green had a moment in 2021, and the good news is the color will be big this year, too.

For a Monochromatic Fit

outfit 5

Design by Tiana Crispino

Styling a monochromatic look is perfect for when you want to look on-trend and put together. Pair patent boots with a matching mini sweater dress and coordinating cloud clutch.

With a Leather Jacket

outfit 6

Design by Tiana Crispino

I saw someone on Byrdie wearing cargo pants and knee high boots, so I bought cargo pants and knee high boots. But seriously, cargo pants are going to be everywhere this spring, and what better way to style them than with black knee-high boots and a biker jacket?

With Baggy Pants and a Bodysuit

outfit 7

Design by Tiana Crispino

Think of channeling Hailey Bieber when rocking baggy jeans and patent boots. Grab your favorite boyfriend jeans and style them over a bodysuit to compliment the oversized look.

With a Mini Skirt and Sweater

outfit 8

Design by Tiana Crispino

A classic pair of brown knee-high boots can be styled so many different ways, but we're channeling Clueless and styling them with a mini skirt and a cropped sweater. For a look like this, a lower heel or block heel may work better than a slinky stiletto.

With a Long Trench Coat

outfit 9

Design by Tiana Crispino

Crocodile-embossed leather boots are versatile and go well with dresses or denim for a variety of looks. We've paired these with high rise skinny jeans and a long trench coat for a sleek work-to-play look.

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