Black Knee-High Boots Are My Holy Grail—Here Are 8 New Ways I'm Wearing Them

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When I say black knee-high boots are my holy grail, there is no exaggeration in my bold statement. Surviving colder weather while also looking cute starts with this exact shoe style. I think I've worn my favorite pair a billion times, and they're still as good as new. One of my surprisingly favorite ways to wear mine is tucked into a wide-leg pair of blue jeans. This is a genius hack to keep your legs warm and also alludes to longer legs. When you find a pair that you can walk for miles in, you will be just as enamored.

I'll get you there today with a quick browse of my picks that—I must say—are pretty darn good. In some ways, you can never truly have enough pairs because there's always something new to love on the horizon. Whether it's Western-inspired boots, rubber stompers, or the elegant stiletto staple, each serves a completely different purpose. I, for one, alternate between my forever classic and exciting cowboy boots, depending on the occasion. Scroll on to discover your new favorite pair of black knee-high boots and outfit ideas that will help you make the most of them. 

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Classic Blazer + Midi Dress + Knee-High Boots
(Image credit: @_sierramayhew)

Speaking of my favorite pair, they're so good I have to show them off on every corner. Oh, and they were under $250.

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Cream Coat + Black Knit Dress + Knee-High Boots
(Image credit: @sylviemus_)

Something about this outfit perfects the cool-girl aesthetic. All you need are the below pieces, a slicked-back bun, and morning coffee to capture the same energy.

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Oversize Knit + Miniskirt + Knee-High Boots
(Image credit: @emmaleger)

If you want to channel the preppy look without overdoing it, this is exactly where to begin. An oversize knit with a fun miniskirt does just that.

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Athleisure Onesie + Standout Blazer + Knee-High Boots
(Image credit: @simplytandya)

An unexpected combination of items sometimes just makes sense. In the case of this tailored blazer and athletic attire, this is true.

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Bright Coat + Iconic Basics + Knee-High Boots
(Image credit: @scoutthecity)

Every season, I love to stake my claim on a statement coat to bring a bit of excitement to winter days. A hot-pink one will do just the trick.

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Sultry Slip + Classic Bag + Knee-High Boots
(Image credit: @meccajw)

The ultimate night-out look has arrived. It's the definition of 2022 elegance.

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Leather Blazer + Fun Mini + Knee-High Boots
(Image credit: @gracecarolinelarcade)

I loved experimenting with fun dresses this summer, and it's exciting to know that we can just keep on wearing them. This is how I'd do it.

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Baseball Hat + Tweed Jacket + Knee-High Boots
(Image credit: @styleheroine)

An unexpected combination always gets people talking. If you love compliments, try copying this fun look.

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Up Next: The Coolest Boots Right Now Are All Coming From These 10 Brands

Associate Editor

Sierra Mayhew was always destined to work in fashion, but she didn't know it at first. Growing up with no choice but to wear a rotation of school uniforms and activewear, her love for fashion really blossomed when she moved away for college and was able to finally define her very own personal style. Shortly thereafter, she interned at Elle magazine and instantly knew that editorial was for her. After graduating from the University of Notre Dame, she worked for ShopBazaar, contributing regularly to Bazaar.com, and finally made her way to Who What Wear, where she is an associate editor. When she’s not working, you can catch her always trying to catch a flight, rollerblading through New York City traffic, or exploring the latest luxury vintage boutique.