• Fashion
  • Beauty
  • Lifestyle
  • Men's Style
  • All
  • Trending
  • Style Stories
  • Style Tips
  • The Edit
  • All
  • Beauty Review
  • Beauty Trends
  • How To
  • All
  • Food
  • Home Decor
  • Gift Guides
  • All
  • Trending
  • What To Wear
  • Iconic Men
  • Mr Jones
David Jones

How to Wear Knee High Boots

When cooler weather arrives, a certain group of skirt-loving women weigh up their options every winter — brave it with bare legs or pull on boring black tights? The fact is, there are some of us who dread the thought of tights, with memories of school uniforms, laddered legs, and waists that are too high and too tight. 

The solution? Knee high or over-the-knee boots. Covering the lower half of the leg and sometimes up to mid-thigh, tall boots give you the warmth of tights but infinitely more stylish. And compared to their shorter cousin, the ankle boot, they create the illusion of mile-long legs and a more streamlined silhouette.

The key to wearing them this season is with a skirt or a dress, as seen in the chic Parisienne streetstyle looks below. Here's three ways to style it, whether it's to the office, a winter festival, or a casual Sunday brunch.

Office Appropriate

Keep it sleek for the office with knee high boots with a pointy toe and stiletto heels. Pair with a mid-length pencil skirt, a peplum jacket and a structured bag.

  • 1

    Coolboot by Stuart Weitzman

    Sexy and chic, these up-to-the-knee pointed-toe boots tick all the boxes.

    Shop Now
  • 2

    Romi Boot by Milana

    These boots are designed with a slim fit for sleek and elegant styling.

    Shop Now
  • 3

    Ucoa boot by Edward Meller

    These Italian-made boots are available in three colours for unlimited styling options.

    Shop Now

Festival Ready

An over-the-knee boot is perfect for a bohemian-influenced festival look. Layer it up with this season's trending poncho or cape, and a mini skirt.

  • 1

    Flat Over the Knee Boot by Tony Bianco

    Flat boots in luxe black leather is perfect for any festival look.

    Shop Now
  • 2

    Highland Thigh High Boot by Stuart Weitzman

    An over the knee boot in stretch suede with a back tie, as pictured in the street style image above.

    Shop Now
  • 3

    Mainline Boot by Stuart Weitzman

    An internal wedge gives these boots a boost without sacrificing comfort.

    Shop Now

Weekend wear

A weekend winter look calls for flat knee high boots. Wear with a tunic and a belt for casual ease.

  • 1

    Aretha Boot by Diana Ferrari

    Mini ankle straps and contrasting brown leather upper give these boots interesting detail.

    Shop Now
  • 2

    Guard Boot by Stuart Weitzman

    Quilted detailing give these boots a casual equestrian feel.

    Shop Now
  • 3

    Liberty Boots by Edward Meller

    Charcoal suede is a great weekend alternative to tan or brown.

    Shop Now