Thigh-High Roller! How To Wear Fall's Sexiest Boot

Photo: Maria Valentino/ MCV Photo.
9-5Thigh-high boots are a tricky proposition in the office. Keep the gam bonanza to a minimum by pairing them with a mid-length kilt, so just the tiniest peek of leg shows when you walk. It’s a downright demure look that even your cubicle-mate (you know, the one with all the cat calendars) will like.
date-nightA '60s-sweetheart shift gets a welcome dose of tough, courtesy of Reed Krakoff’s stacked-sole boots. We think Alexa would approve.
weekend-warriorThis one’s for advanced over-knee enthusiasts only: Tibi’s daringly high, stirrup leather leggings. Pair them with a short, swingy dress that makes the most of their height — it’s all about that flirty flash of thigh.
after-hoursOver-the-knee boots, lace, and a leather mini — oh yeah, we’re going there. The elegantly dark palette and a loose, scalloped-hem top keep the look from veering into Pretty Woman territory.
Check out Trend Tracker for more genius ways to wear our favorite fall trends.
Illustrated by Katelyn Kappel.

R29 Original Series

Watch Now
Hey Hollywood - you can't win without women. We helped 12 female directors claim their power.
Watch Now
In fashion, what's seen on the streets is just as important as what goes down the runway.
Watch Now
The craziest trends, most unique treatments, and strangest subcultures in the beauty world.
Watch Now
A premiere series about the important moments, powerful women and pressing issues of our time.