Looking back at my high school photos is a borderline jump scare. 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 leggings with a boatneck sweater, an infinity scarf, and—you guessed it—a pair of knee-high riding boots. I’d argue that it’s still a tried-and-true look (skinny jeans are back), but I’ve also since learned there are so many more styling possibilities than whatever I was regurgitating from Tumblr.
The biggest myth about wearing knee-high boots that I’ve since unlearned, for example, is the idea that they can only be worn in the fall or winter. In fact, this summer in particular has seen countless celebrities and street style stars proving that wearing tall boots in hot weather is absolutely a thing. Take Anne Hathaway and Suki Waterhouse: Both recently stepped out in suede footwear that somehow felt light and airy, while Chloe Bailey and Madonna showed us how to make black leather boots and punk styling work year-round.
These celeb looks also shut down another false idea: that knee-high boots don’t work with very many bottoms. If anything, they actually go with everything, from miniskirts to capri pants and beyond. 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.
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