Looking back at my high school glamour shots (read: self-timer photos in my backyard) is a borderline jumpscare. This was before I figured out how to style knee-high boots for my personal style, so I simply mimicked whatever was “in” at the time. I looked like a hipster Caitlin Covington cosplaying Christian Girl Autumn in dark wash skinny jeans (or leggings) with a boatneck sweater, an infinity scarf, and—you guessed it—a pair of knee-high riding boots. At the time, it was the only outfit I knew how to put together with my beloved Steve Madden shoes. And while I’d argue that it still is a tried-and-true look, I’ve since learned there are so many more styling possibilities than whatever I was regurgitating from Tumblr.
The biggest myth around wearing knee-high boots is that they don’t work with a lot of bottoms. Now, I would challenge that they actually go with any bottom, from mini dresses to long jorts, midi and maxi skirts, and more. Whether your personal style leans more preppy, sporty, classic, or anything in between, there are endless iterations of tall boot styles that fit the latest fashion trends and match with your wardrobe.
Ahead, find 9 outfit ideas and inspo for how to style knee-high boots, plus more styling tips and tricks to get the looks for yourself using items in your closet.
Classic Knee-High Boots + Matching Set
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