How to Style Knee-High Boots—6 Fall-Ready Outfit Ideas

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Photographed by Phil Oh

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When it comes to winter weather, boots are the obvious footwear of choice. Chic with almost any outfit and protective against the cold, they’re among the most versatile of wardrobe staples. Knee-high boots, however, can occasionally leave a sartorialist feeling stumped. Even though they’re as easy to wear as their lower-cut counterparts, knee-high boots definitely bring a bit more drama to any ensemble, making them slightly more intimidating to style.

The Best Knee-High Boots, According to Vogue:

Luckily, our guide is here to quell any fears, with six foolproof and original ways to incorporate knee-highs into your own look. Whether you’re doubling up on leather with a coordinating midi-skirt, leaning into minimalism with a full monochromatic look, or going mod with a cute mini, these chameleon-like boots will be your new best friend, especially as we enter the colder months. Check out how we’d wear them, below.

The Leather-On-Leather Look:

Leather riding boots and a leather midi skirt are an unexpectedly chic (and warm) combination for the colder months ahead. Layer a white button-up under a sweater on top, for a bit of added texture.

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Citizens of Humanity

Kayla oversized shirt

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Alex Mill

Nottinghill sweater

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Aeyde

Henry knee boots

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Cos

pleated midi skirt

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Completedworks

silver-plated bangle

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Kassl

Oil tote bag

The Micro-Mini Look:

Go mod, but make it modern, by pairing a classic mini and boots combo with an of-the-moment knit and denim barn jacket.

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J.Crew

denim barn jacket

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Bally

jacquard-knit sweater

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Reformation

Raven knee boots

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Liberowe

Vera mini skirt

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Mansur Gavriel

Gaia shoulder bag

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Agmes

Laila hoop earrings

The Maxi-Dress Look:

Pair these sumptuous chocolate brown boots with a soft dress and jacket in the same shade. We love black accessories for a subtle bit of added contrast.

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Fforme

Ainsley ribbed maxi dress

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Massimo Dutti

short jacket

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Madewell

Shopper tote bag

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Wilfred

wool scarf

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Tabayer

Oera earrings

The ’90s Denim Look:

It doesn’t get more classic than jeans, a blazer, and a sleek pair of knee-high boots. You’ll wear this timeless look for years to come.

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The Row

Timoty double-breasted blazer

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Joseph

t-shirt

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Proenza Schouler

Bronco knee boots

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Agolde

90s Pinch Waist jeans

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Madewell

Perfect leather belt

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Alighieri

The Ancient Incantations pinky ring

The Autumnal Hues Look:

Brown suede pairs well with slightly-off colors in the same family, like burgundy and khaki, and mixed textures, like lace and soft leather, making for a compelling look.

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Staud

Wally knee boots

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Co

belted leather jacket

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Aritzia

cashmere relaxed crew sweater

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Our Legacy

Clasp frayed midi skirt

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Banana Republic

boyfriend t-shirt

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Lié Studio

The Elizabeth earrings

The All-Black Look:

Another classic knee-high boot pairing is a pair of slim black trousers. Lean into the minimalism of this look by adding a wrap coat and sweeping your hair back into a French twist.

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Nour Hammour

Cora belted padded coat

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The Frankie Shop

Rafaela oversized sweater

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Khaite

Davis boots

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Veronica Beard

Stila cropped pants

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Bleue Burnham

Freshly Cut Lawn ring

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Machete

French hair pin