6 Knee-High Boot Outfit Ideas to Testdrive This Fall | Vogue

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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.

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.

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.

Citizens of Humanity

Kayla oversized shirt

MODA OPERANDI

Alex Mill

Nottinghill sweater

ALEX MILL

Aeyde

Henry knee boots

NET-A-PORTER

Cos

pleated midi skirt

COS

Completedworks

silver-plated bangle

NET-A-PORTER

Kassl

Oil tote bag

BERGDORF GOODMAN

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

J.Crew

denim barn jacket

J.CREW

Bally

jacquard-knit sweater

NET-A-PORTER

Reformation

Raven knee boots

REFORMATION

Liberowe

Vera mini skirt

NET-A-PORTER

Mansur Gavriel

Gaia shoulder bag

SHOPBOP

Agmes

Laila hoop earrings

NET-A-PORTER

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.

Fforme

Ainsley ribbed maxi dress

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Toteme

leather knee boots

NET-A-PORTER

MODA OPERANDI

Massimo Dutti

short jacket

MASSIMO DUTTI

Madewell

Shopper tote bag

SHOPBOP

Wilfred

wool scarf

ARITZIA

Tabayer

Oera earrings

NET-A-PORTER

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.

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

MADEWELL

Alighieri

The Ancient Incantations pinky ring

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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.

Staud

Wally knee boots

NET-A-PORTER

Co

belted leather jacket

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Aritzia

cashmere relaxed crew sweater

ARITZIA

Our Legacy

Clasp frayed midi skirt

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Banana Republic

boyfriend t-shirt

BANANA REPUBLIC

Lié Studio

The Elizabeth earrings

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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.

Nour Hammour

Cora belted padded coat

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The Frankie Shop

Rafaela oversized sweater

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Khaite

Davis boots

KHAITE

Veronica Beard

Stila cropped pants

VERONICA BEARD

Bleue Burnham

Freshly Cut Lawn ring

NET-A-PORTER

Machete

French hair pin

MACHETE