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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

$40

Universal Thread

Bromley Over the Knee Riding Boot

$159

Michael Kors

Tempest Over The Knee

$950

Tamara Mellon

Grand Ambition Huntington Over-the-Knee Boot

$205

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

$225

Jeffrey Campbell

Black Patent Leather Above-The-Knee Boot With Heel

$330

Albano

Faux Patent-Leather Over-the-Knee Boots

$1,995

Saint Laurent

Liney Boot

$90

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

$597

Rag & Bone

Kate Flat Over the Knee Boots

$72

Asos Design

Emilie Thigh High Boot

$1,165

Stella McCartney

Haleen

$229

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

$995

Clergerie

Rockstud Knee High Boot

$1,595

Valentino Garavani

Shale

$80

Volatile

Plannia

$161

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

$141

Marc Fisher Ltd.

Sidney Microsuede Over the Knee Fashion Boots

$40

A New Day

Tieland Over the Knee Boot

$718

Stuart Weitzman

Faux Suede Over-the-Knee Boots

$42

Forever 21

Suede Over-the-Knee Boots

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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.

Calypso

$130

Sole / Society

Wasi Over the Knee Boot

$112

Louise et Cie

Canyons Over the Knee Boot

$100

Chinese Laundry

Pitch Wide Calf Thigh High Boot

$45

Journee Collection

Textured Over-the-Knee Boots

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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

$158

Silent D

Logan Over the Knee Boot

$225

Kelsi Dagger Brooklyn

Elyse Tall Boot Slouch

$200

Free People

Lila 90 mm Knee Boot

$628

Tory Burch

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