6 Knee-High Boot Outfit Ideas to Testdrive This Fall

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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:

• The Brown Riding Book: Aeyde Henry knee boots, $795
• The Classic Black Suede: Reformation Raven knee boots, $498
• The Slick Kitten Heel: Toteme leather knee boots, $1,190
• The Modern Cowboy: Proenza Schouler Bronco knee boots, $1,295
• The Carmel-Colore Pick: Staud Wally knee boots, $495
• The Cool-Girl Boot: Khaite Davis boots, $1,350

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.

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.

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.

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.

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.

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.