How to Style Knee-High Boots—7 Fall-Ready Outfit Ideas

When it comes to fall 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 even the most sartorially-savvy feeling stumped. While some might argue 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 on how to style knee-high boots, with seven foolproof and original ways to incorporate them into your own look. Whether you’re doubling up on leather with a coordinating midi-skirt, leaning into minimalism with a full monochromatic moment, or going prep with a pleated 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.

With a Midi Dress and Riding Boots

A white dress is cool-weather-ready when paired with heavy riding boots and a chunky knit.

With a Turtleneck and Printed Suede Midi

Leather riding boots and a printed suede midi skirt are an unexpectedly chic (and warm) combination for the colder months ahead. Keep the rest of the look simple with a slim turtleneck on top.

With a Mini Skirt and Peacoat

Go preppy, but make it modern, by pairing a classic pleated mini and boots combo with an of-the-moment knit and cropped peacoat—one of winter’s top coat trends.

With Denim and Blazer

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.

With a Midi Skirt and Relaxed Bomber Jacket

Pair these sumptuous chocolate brown boots (the hue of the moment!) with soft separates and a leather jacket in the same shade. We love a slouchy leather bomber with this look.

With Slim Trousers and a Chore Coat

Another classic knee-high boot pairing is a pair of slim black trousers. Lean into the minimalism of this look by adding a trim white button-up and field jacket.

With All Black

Almost-burgundy brown leather pairs particularly well with black, for a more interesting pop that still feels neutral and easy to wear.