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.