What to Wear with Knee High Boots

15 October 2025

As temperatures drop and leaves begin to fall, knee-high boots return to the spotlight as the season’s must-have item. They’re stylish, practical, and endlessly versatile, bridging the gap between fashion and functionality - is there anything better for the colder months?

Unlike other seasonal shoes that might be limited to specific settings or styles, knee high boots can be dressed up or down, worn over or under trousers, and paired with everything from dresses to jeans. They’re a timeless investment piece that never truly goes out of fashion, making them a smart addition to your cold-weather wardrobe.

In this guide, we’ll walk through several outfit ideas that showcase just how versatile knee-high boots can be. You’ll also find top styling tips to help you make the most of this essential seasonal footwear and step into the season with confidence.

Here's what we'll cover:

Why knee-high boots are an autumn-winter essential
7 autumn-winter outfit ideas for knee-high boots

Autumn-Winter Essential: Knee High Boots

Knee-high boots are a staple of cold-weather fashion for good reason. Their tall silhouettes help them to trap warmth, keeping your feet warm on even the chilliest days, while their sturdy construction can handle whatever weather autumn and winter might throw at them. And unlike many shoes that leave your ankles exposed or struggle with slippery terrain, knee-high boots offer full coverage and a dependable grip.

In addition to their practicality, these boots are super versatile from a styling perspective. Whether you're heading to the office, out for a casual walk, or attending a seasonal event, there's a knee-high boot that fits the occasion. They also work just as well with classic and experimental looks, without compromising on warmth or comfort.

From classic leather, sleek suede, or statement prints, knee-high boots add polish to any autumn-winter outfit while keeping your legs warm and protected from the elements.

7 Autumn-Winter Outfit Ideas for Knee High Boots

There are endless ways to wear knee-high boots, whether you're going for laid-back weekend looks, work-friendly ensembles, or something more elevated. The key is to balance proportions and play with textures, so your boots complement the rest of your outfit rather than competing with it.

Here are 7 of our favourite autumn-winter outfit ideas.

1. Skinny jeans and a knit jumper

This classic pairing is the foundation of lots of winter looks. Find a pair of slim or skinny jeans that can tuck comfortably into your boots and combine with a chunky knitted jumper for a cosy yet stylish vibe.

Add a long wool coat and scarf to the mix for extra warmth and texture. Brown leather knee-high boots work particularly well with blue or black denim, offering contrast and a touch of rustic charm.

Finish the outfit with a leather tote or structured handbag to elevate the look.

Try the look with brown knee-high boots

2. Sweater dress and tights

For a comfortable, feminine outfit ideal for weekend brunches or casual evenings out, pair your knee-high boots with a knitted jumper dress and opaque tights. This combo is chic and warm, perfect for the winter season. Choose black boots with a block heel for an elevated finish or go with flat styles for maximum comfort. Layer with knee-high socks inside your boots to add extra warmth and cushioning.

Play with texture by adding a belt or faux-fur gilet to break up the silhouette and add some visual interest.

Try the look with black knee-high boots

3. Midi skirt and tucked-in blouse

Midi skirts are perfect for bringing visual balance to the height of knee-high boots. Pick a pleated or A-line midi that falls just below the knee, and pair it with a tucked-in blouse or turtleneck.

This outfit works well for both office wear and smart casual events, with leather boots in neutral shades like beige, grey, or oxblood being a good choice for a sophisticated touch.

Layer with a cropped jacket or smart blazer to create a flattering silhouette and a polished finish.

Try the look with smart leather boots

4. Leggings and oversized layers

Practical and stylish, leggings combined with baggy shirts, cardigans, or ponchos create a relaxed silhouette that still feels polished when anchored by knee-high boots. This is a great casual look that prioritises comfort: great for those cold days where you’d rather do anything than go outside.

Black boots are a versatile choice here, but don’t be afraid to experiment with colour or texture. Consider adding statement jewellery or a bold lipstick to elevate this relaxed look for casual outings.

5. Tailored shorts and a blazer

Extend the life of your tailored summer shorts by pairing them with knee-high boots and opaque tights. Bring a fitted or oversized blazer to the mix for a smart, structured look that’s perfect for less-than-ideal weather.

Stick to darker tones for a streamlined outfit, or introduce shades like burgundy, forest green, or navy to evoke the season. You can also add a fine-knit turtleneck or blouse underneath the blazer for a touch of elegance and added warmth.

6. Maxi coat and tonal layering

For a sleek, modern silhouette, choose a monochrome or tonal colour palette and layer longer pieces like a maxi coat over slim trousers or a midi dress. Knee-high boots in a matching or complementary colour extend the legs visually and pull the outfit together seamlessly.

This minimalist, fashion-forward approach works well with understated accessories and neutral makeup for a clean finish.

7. Slip dress and leather jacket

For a touch of edgy feminine styling, pair a floaty slip dress with a leather jacket and knee-high boots. This look is great in early autumn when the weather is just beginning to turn. Add tights as needed and consider boots with a chunky sole for contrast.

A crossbody bag or statement earrings can add the final touch to perfect this look for a night out.

Explore Our Long Boots Collection

Ready to find your perfect pair? Our Knee-High boots collection features a wide range of styles to suit every taste, from polished leather to soft suede, flat soles to high heels. Whether you're dressing for workdays, weekend walks, or winter adventures, there's a pair of knee-high boots waiting to complete your outfit.

If you're unsure which style is right for you, contact our team or pop into your local store for personalised advice and fittings. Our experts are always happy to help you find the perfect match for your wardrobe and lifestyle.