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How to Wear Over-the-Knee Boots This Winter

If you must venture out—and want to look professional when you do—pair black over-the-knee boots with a jewel-tone sweater dress and a matching belt. A slit in the skirt shows off your footwear and helps you hit your stride.

Gretal Boots


Universal Thread

Bromley Over the Knee Riding Boot


Michael Kors

Tempest Over The Knee


Tamara Mellon

Grand Ambition Huntington Over-the-Knee Boot


Cole Haan

Patent Leather Over-the-Knee Boots

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Shiny, patent-leather over-the-knee boots feel a little bit flashier than a standard pair. Have fun with yours: Wear them with unexpected layers—with playful pastel accessories, opaque tights, and a boxy, outsize blazer, no one needs to know if you slept in the T-shirt and hoodie.

Break Thigh High Boot


Jeffrey Campbell

Black Patent Leather Above-The-Knee Boot With Heel



Faux Patent-Leather Over-the-Knee Boots


Saint Laurent

Liney Boot


Jessica Simpson

Platform Over-the-Knee Boots

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A platform upgrades over-the-knee boots to a wear-them-everywhere staple. Regardless of heel height, if your foot is more or less flat, you can clock miles comfortably—even if they’re all within a couple blocks of your home.

Scout Boot


Rag & Bone

Kate Flat Over the Knee Boots


Asos Design

Emilie Thigh High Boot


Stella McCartney



Franco Sarto

Moto-Inspired Over-the-Knee Boots

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Pick a over-the-knee boots that will give your mini dress some edge: Biker-style details (buckles, studs, lug soles—or all three at the same time) are very on trend for 2021.

Bellaa 4



Rockstud Knee High Boot


Valentino Garavani






Ted Baker

Drawstring Over-the-Knee Boots

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If you’ve shied away from over-the-knee boots because you don’t like the way they pool around your quads, there’s an on-trend solution: over-the knee boots with a drawstring keep things streamlined.

Octavie Over the Knee Boot


Marc Fisher Ltd.

Sidney Microsuede Over the Knee Fashion Boots


A New Day

Tieland Over the Knee Boot


Stuart Weitzman

Faux Suede Over-the-Knee Boots


Forever 21

Suede Over-the-Knee Boots

Kirstin Sinclair / Getty

When in doubt, try monochromatic dressing. Start with suede over-the-knee boots, and match your layers (even your outerwear) for an one-color look.



Sole / Society

Wasi Over the Knee Boot


Louise et Cie

Canyons Over the Knee Boot


Chinese Laundry

Pitch Wide Calf Thigh High Boot


Journee Collection

Textured Over-the-Knee Boots

Melodie Jeng / Getty

Breathe new life into a floral dress with textured over-the-knee boots. Whether the pattern is subtle or high-impact, the contrasting fabrics will make an any-old-day office dress feel extra sophisticated.

Comess Velvet Knee-High Boots


Silent D

Logan Over the Knee Boot


Kelsi Dagger Brooklyn

Elyse Tall Boot Slouch


Free People

Lila 90 mm Knee Boot


Tory Burch

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