
Photo: Marko Metzinger/Studio D
Q: Can I wear over-the-knee boots without looking like I'm in Pretty Woman?
A: Certain permutations of this trend—like thigh-high and stiletto versions—can indeed resemble streetwalker apparel. But boots that end above the knee, with flat or chunky low heels, are upscale and cool. How to pull them off: Pair with appropriately cut skirts and dresses, and match their color to your tights or leggings as closely as possible. If you want to wear this style with jeans, gray-toned pairs blend nicely. Remember: Your top or jacket should fall past your hips, or else the look can be tacky.See Adam's picks for great over-the-knee boots

Vertical studding creates a long leg line—add black tights. (Stuart Weitzman, $675, Bergdorf Goodman, NYC; 212-753-7300)

On the weekends you'll feel good walking around in this supple, 100 percent vegan pair. (Cri de Coeur, $150; Endless.com)

Pulled on with dark leggings and a chunky sweater, this embellished style is casually fashionable. (Tory Burch, $650; ToryBurch.com)

Buttery soft leather molds to your legs and can be worn over the knee or just below. (Daniblack, $350; Zappos.com)

These Geren Ford boots are just as functional as they are fashionable. The zippered sections can be zipped off to create four different looks and heights. (Geren Ford, $499; Bleu Clothing, (323) 939-2228)

Pair these bright-colored boots with black or neutrals to let them be the star of the show. (Colin Stuart, $189; VictoriasSecret.com)
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