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.