The Dresses, Skirts and Trousers That Look Best With Knee-High Boots

For the longest time, I was hopelessly devoted to ankle boots. I'm petite, and I always assumed that anything above the calf would make my legs look out of proportion with the rest of my frame. Yes, even fashion editors can get tunnel vision. However, maybe four years ago, I invested in a pair of black, buttery-leather knee-highs with a block heel and almond toe. Slipping them on for the first time, I'd never felt chicer.

Fast-forward to 2022, and I have a few pairs of knee-high boots that I've come to rely upon when the temperatures dip. I have a beige suede pair complete with a wooden heel, a mock-croc burgundy pair with a subtle patent finish, and my OG black leathers, all of which I get so much wear out of. Initially, however, I found styling them a bit of a challenge. Yes, they look great worn under floaty dresses, but I wanted to expand my options. So I headed straight to Instagram and began saving down my favourite looks involving knee-high boots.

Now with autumn in full swing, I've been updating my Saved folder with new outfit ideas to try, and I couldn't help but notice how many of them centred on knee-high boots. So I decided to share them with you should you also find yourself wondering what to wear with knee-high boots. Scroll on for the answer.

1. Leggings

Style Notes: If, like me, you always love the trousers-tucked-into-boots look on other people but are looking for an easy gateway to start with, allow me to present to you this legging-and-knee-boot combination from Marilyn. Sticking to a black-and-white palette instantly elevates this ensemble. 

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2. Minidresses

Style Notes: Mini hemlines were all over the runways, with countless designers styling them with knee-high boots. I get it—it really does add a cool, nonchalant vibe to a minidress that might otherwise look ultra glam. 

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3. Skinny Jeans

Style Notes: Once you've mastered the art of styling leggings and knee boots, protect yourself from the elements even further with a pair of skinny jeans. The thicker material is ideal for cooler days, while the silhouette will slip under the majority of knee boots. 

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4. Thigh-Split Dresses

Style Notes: Chances are, if you've just treated yourself to a new pair of boots, you'll want to show them off at any given opportunity. So why not showcase them with a thigh-split dress that shows a flash of your boots every time you step?

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5. Tailored Trousers

Style Notes: That's right. Fashion's finest have even begun tucking their tailored trousers into their knee-high boots, and I'm surprised at just how much I love this look, too. Look for soft fabrications that will fold more neatly under your boot. 

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6. Miniskirts

Style Notes: For a chic daytime look, style a miniskirt you'd ordinarily save for nights out with a pair of chunky and flat knee-high boots—a combination that kept cropping up on my Instagram deep dive. 

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7. Soft Jeans

Style Notes: If skinny jeans aren't your thing, then rest assured you can also achieve the look with a straight-leg pair. Much like with tailored trousers, look for the softest denim you can find and seek out boots with a slightly wider calf; a pair of on-trend cowboy boots will do the trick! 

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Next Up: It's Boot Season, and These Are the Trends That Will Dominate