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

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    Photo: Maria Valentino/ MCV Photo.
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    Thigh-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-night

    A '60s-sweetheart shift gets a welcome dose of tough, courtesy of Reed Krakoff’s stacked-sole boots. We think Alexa would approve.

    weekend-warrior

    This 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-hours

    Over-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.

    Market Research by

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