Let’s start by giving credit where credit’s due: When it comes to the over-the-knee-boot trend, Julia Roberts in “Pretty Woman” deserves some serious props. Who could forget her star-making turn as hooker-with-a-heart-of-gold Vivian Ward, who meets the man of her dreams while rocking patent leather thigh-highs? In 1990, those shoes were shocking—and laughably indicative of prostitution—but in 2016, up-to-there footwear is par for the course, and totally wearable for day or night. In fact, these days, figuring out how to wear over-the-knee boots is practically a no-brainer.
Whether you wear a flat suede pair with a mini-skirt in lieu of tights (while the weather permits) or hike up some high-heel leather ones over your skinniest skinny jeans, over-the-knee boots are actually some of the most versatile shoes in your wardrobe for fall and winter.
In the gallery, see 33 new ways to wear them right now, inspired by our favorite bloggers.