17 Thigh-High Boot Outfit Ideas Anyone Can Pull Off

Just go for it.

Thigh High Boots
(Image credit: Christian Vierig)

The thigh-high boot is a dramatic shoe. There's something provocative, but also stylish, about the silhouette. Julia Roberts in Pretty Woman rocked them amazingly well—but if pre-makeover Vivian Ward isn't exactly the vibe you're going for on a Monday morning, nay, even a Saturday night, we understand. We've found 17 work- and weekend-appropriate ways to wear the shoe without shoving you completely out of your comfort zone. (The easiest outfit to throw together? Your favorite top, jeans, and the killer leg-skimming boots.) Thigh-high styles can look elegant, not tawdry, when styled with the right fall/winter pieces. (And if you need to stock up on said fall items, here you go.) Using a little street style inspo, below, we'll show you how to put items you already own together for a cohesive, fashion girl-approved ensemble. We even provided similar boot options to shop just in case you don't have a pair, or need a new one.

Marina Liao is the former fashion news editor at MarieClaire.com, where she covers celebrity style (from Meghan Markle to Katie Holmes), fashion trends, and shopping advice, plus conducts original interviews with industry insiders.