Thigh-high boots can go from classy to trashy faster than you can polish off a Nutella donut—and that’s a mere matter of seconds. And although we love, love, love Julia Roberts’ iconic role as a hooker with a heart of gold in 1990’s Pretty Woman, those slouchy pleather boots scream fashionably unstable. But fall’s latest take on the tall boot trend has us (and style mavens like the always chic Miroslava Duma) slightly more at ease—though we’re sure there are still some Pretty Woman imposters ominously circulating around the internet.
Check out these modern, sophisticated (yes, thigh-highs can be sophisticated!) versions that—to be totally honest—are definitely necessary for your fall footwear wardrobe.
Charles by Charles David Jettison Over the Knee Boot: These two-tone thigh-highs are the perfect beginner’s boot for the over-the-knee nervous crowd. Start out wearing them with black skinnies and a simple crewneck sweater or blouse-and-blazer combo. Then, when you’re ready for the sartorial challenge, try them with a printed skirt and turtleneck a la Miroslava Duma (who knew thigh-highs had such ladylike potential?).
ALDO Dyanna Boot: Possibly the closest (least lady of the night-ish) version of Vivian’s Pretty Woman boots any woman should be allowed to own. These patent leather Aldo thigh-highs are sleek and sexy—but, again, not too sexy.
Vince Camuto Baldwin Over the Knee Boot: These sandy-colored suede boots dubbed Mouse Grey—whatever that means—are the perfect partner for your favorite blue jeans (light wash, dark, or any medium in between). Just picture them now with your trusty blues, a white tee, and navy blazer. Perfection.
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The taller the boots the better!!