Mastering Over-the-Knee Boots: Fall 2023 Style Guide

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Over-the-knee boots are the Beyoncé of boot styles. Unapologetically bold and eye-catching, they demand attention every time they’re out. Wear a pair with your simplest gray hoodie and you’re a street-style superstar. Wear them with a statement minidress and at least one passerby will have to shield their eyes or risk being blinded by your fashion brilliance. They are, simply put, iconic. They also can be pretty difficult to wear.

Finding over-the-knee boots that fit can be a challenge in and of itself. Shopping for a pair is basically like shopping for jeans that also fit your feet. And despite the many curvy women, famous or otherwise, who love a pant-boot moment, there are shockingly few brands that design over-the-knee boots for folks whose thighs are thicker than their calves. But when you find a pair that does fit — our recs here! — slipping (or yanking) on a pair of over-the-knee is a magical fashion moment, matched only by the OOTD looks you can create with them.

Finally, Trendy Over-the-Knee Boots Made Specifically for Thick Thighs

Ahead, we’ve rounded up 10 ways to wear over-the-knee boots that will make the odyssey of finding the right pair well worth the effort. If, as this writer firmly believes, these boots are the Beyoncé of footwear, then the ‘fits below are your VIP ticket to the Renaissance tour (well, not actually, but you get it).

In Lieu of Pants

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The very thing that makes shopping for over-the-knee boots such a hassle, is what makes them such a fashion standout: the fit. They’re basically fun pants! Thanks to all the coverage, the right pair can effectively function like pants when worn with a tunic-length top, blazer, or jacket.

With Paperbag Shorts

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Shop Similar: London Rag Flittle Over-The-Knee Boot, $90.Casual, comfortable summer separates like loose-fitting paperbag shorts and lightweight cardigans pair beautifully with over-the-knee boots, especially in an eye-catching print or pattern.

With a Floral Minidress

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Add some edge to an otherwise sweet floral minidress by wearing it with a pair of vampy over-the-knee boots. There’s no one style of thigh-high boot that works best with this look, but we do love the contrast of a floral print and shiny vinyl.

As a Pop of Color

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Shop Similar: Stuart Weitzman Ultrastuart 100 Stretch Boot in India Pink, $950.We’re not saying that you should drop cash money on a pair of Barbiecore thigh-high boots, but we are saying that having a pair of over-the-knee boots in a vibrant shade of yellow, blue, or bubblegum pink can transform even your most basic skirts and dresses.

ALDO Just Dropped the Ultimate Barbie Shoe CollabWith a Tunic

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Shop Similar: Paris Texas Leather Over-the-Knee Boots, $1,030.Snuggly and chic, this ‘fit can be as minimal or as over-the-top as you like. A long, vintage graphic tee you’ve worn for years as a sleep shirt works just as well as a lace tunic dress, like Heidi Klum’s.

With an Oversized Hoodie

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Another sneakily cozy over-the-knee boots look, this ‘fit has a street-style vibe that demands opulent accessorizing. From high-end streetwear statement bags to tattoo-artist inspired designs and embroidery, don’t be afraid to be absolutely extra.

Instead of Stockings

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Shop Similar: Gedebe Logan Cuissarde Thigh-High Boots, $1,644.For a high-impact look, swap out thigh-high stockings or tights for a pair of sheer mesh, over-the-knee boots. When accessorizing, opt for textures that bring out the shine in your boots.

Show Off Some Leg

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Dresses with thigh slits were basically made for over-the-knee boots. Even simple silhouettes like a classic shirt dress receive an extra-high dose of flirtiness when worn with thigh-skimming boots.

With a Slip Dress

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Channel your inner off-duty model by wearing over-the-knee boots with a lingerie-inspired slip dress. Celebs like Emily Ratajkowski and Irina Shayk have brought this slinky dress style to our attention and, quite frankly, it slays.

With Preppy Separates

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Shop Similar: Amina Muaddi Jahleel Thigh High Boots, $1,605.There’s no escaping the rise of the preppy aesthetic this year. Even if you never went to a Gossip Girl-esque prep school, you can still achieve this aesthetic’s blend of academia and fashion girlie by wearing preppy separates with a pair of over-the-knee boots.

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