Photo: Marko Metzinger/Studio D

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