What to Wear with Knee-High Boots This Autumn and Winter

You don’t need to be a total fashionista to have noticed that knee-high boots have already earned their place among autumn and winter’s standout styles. Working as hard for the school run as they do for a night out, they’re certainly worth the investment.

  

Whether you go for a sleek leather finish or something with a little more texture, a good pair of knee-high boots will carry you through the whole season.

Skirts and knee-high boots are one of those combinations that just make sense. A reliable look for the transitional seasons, it strikes the perfect balance of comfort and style when it’s too warm for jeans and a winter coat, but too cold for bare legs and a light layer.

 

The good news is this pairing works with almost any silhouette. Mini and midi skirts will show off the boot beautifully, while maxis and flowing boho styles let them subtly peek through for a softer, more relaxed look.

 

For the office, try teaming a column maxi skirt with heeled boots and a jumper or shirt, depending on your office dress code. For the weekend, swap in a leather midi skirt with pointed boots and a soft blouse, or choose a pencil skirt if you’d prefer a slightly more structured shape.

If you’ve invested in a good pair of boots, you don’t want to hide them among floods of fabric. That’s why this season is all about wearing trousers that stop above the ankle, letting the shoes take centre stage.

 

Cropped trousers, culottes and longer shorts all work brilliantly here, especially if you're still a new knee-high boot owner. Just remember to keep everything in one tonal colour palette to help the silhouette read as intentional.

 

While these styles are the easiest way in, knee-high boots aren't only for shorter hemlines. Why not layer them under wide-leg trousers or bootcut jeans for a look that feels comfy and current? These looks will get more wear out of the bottoms already in your wardrobe, too.

For transitional dressing, dresses and knee-high boots are hard to beat. The combination takes your dresses from summer-only statement pieces to all-season staples, and it works for almost all the plans in your diary.

 

For the office, a long-sleeve midi dress pairs with leather knee-high boots for a look that feels smart without trying too hard. Or layer a pinafore dress over a shirt for something with a bit more personality.

 

On the weekend, a flat boot and printed midi dress will keep things relaxed during the day. Later, just swap in a slight heel and clutch bag to take the same look seamlessly into the evening.