Adam Glassman
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
Stuart Weitzman boot

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

Cri de Coeur over the knee boots

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

Tory Burch embellished boot

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

Daniblack over the knee leather boot

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

Geren Ford zipper boot

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)

Colin Stewart boot for Victoria's Secret
Pair these bright-colored boots with black or neutrals to let them be the star of the show. (Colin Stuart, $189;

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