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

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.
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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This kind of blazer is both my night-out and business casual go-to.
The chunky heel must be the secret. My feet never get tired in these.
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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After getting stuck in a pair of boots and having a friend come over to pull me out, I really look for a pair that has a zipper.
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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I love the visible-thong trend, and with a look like this, you can choose to hide or show off the strings.
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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I may or may not have already bought too many blazers to count this season, but this one is too good to scroll past.
Tie together any brown + black outfit with the well-crafted heel on this pair of boots.
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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The ultimate night-out look has arrived. It's the definition of 2022 elegance.
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Take your slips from day to night by choosing a mysterious and dark pattern.
I haven't stopped thinking of this bag since I first laid eyes on it. Now that it's on sale, I might pull the plug.
Worth the splurge.
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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An unexpected combination always gets people talking. If you love compliments, try copying this fun look.
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As soon as I put on a jacket like this, I begin to refer to myself as mademoiselle.
Up Next: The Coolest Boots Right Now Are All Coming From These 10 Brands
Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.
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