How To Wear Thigh-High Boots: 5 Tips for Looking Totally Chic, Not Totally Cheap

Hanah Snavely

Let’s start by giving credit where credit’s due: When it comes to over-the-knee footwear, Julia Roberts in “Pretty Woman” deserves all the glory. Who could forget her star-making turn as hooker-with-a-heart-of-gold Vivian Ward, who meets the man of her dreams while rocking patent leather thigh-high boots? Now that that’s settled, let’s talk about today’s take on the thigh-high trend, which offers a little less flash, a lot less trash, and some major style points for those who dare.

Thigh-high boots hit hard this season, with top designers such as Chanel, Phillip Lim, and Chloë showcasing their own versions on Fall 2013 runways, and now, as the trend trickles down from the catwalk to the masses, it’s key to understand how to pull off the silhouette while still looking high-style.

Whether you’re planning on busting out a dusty pair from the back of your closet, or ponying up to purchase a new set (and if so, have you seen Tibi’s transformative pair?), we’ve nailed down 5 ways to wear thigh-high boots and still look totally chic, as opposed to looking like you’re out trolling for,um, a “date.”

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1. Keep your clothes loose and kinda unflattering. No matter how you slice it, thigh-high boots add a serious dash of sex appeal, and it’s for this reason you can rock an otherwise less-than-figure-flattering dress, like a boxy shift or oversized shapeless sweater, which balances the inherent sexiness of the shoe style.

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2. Dark on bottom, layered on top. If your thigh-high boots are skin tight, be sure to wear them with opaque tights, leggings, or dark skinnies, which leaves you plenty of room to add volume and texture on top. Add color, play with layers, or throw on a bright statement bag.

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3. Stay true to the hue. By working a monochromatic look with your thigh-highs, you draw attention away from the severity of the style, and add a subtle touch of high-fashion drama without screaming it from the rooftops. Extra credit for hue-on-hue layering here, too.

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4. Sock hop. Want to test the waters a bit before you dive in whole hog? Invest in a pair of over-the-knee socks and pair them with knee-high boots of the same color. Throw on a skirt or dress that flashes just a sliver of thigh, layer on a loose cardigan, and even add a beanie for an easy-peasy cool-girl vibe.

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5. Short skirt, long coat. Overcoats and long trench coats  do wonders for thigh-high boots, letting you rock all sorts of short, tight, sexy bottoms if you want to, all the while letting the long cut of the coat slim (and chic up) the look. Just be sure that if you’re going tight on the bottom, keep things looser on the top — the Hervé Léger bandage babe look is better left to the professionals … or never at all with over-the-knee footwear.

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