How to style knee-high boots—6 outfit ideas to wear all year round

Master knee-high boots with these stylish outfit formulas

How to style knee-high boots street style
(Image credit: Getty)

Wondering how to style knee-high boots in a way that looks fresh and contemporary? We’ve got all the inspiration you need with these easy-to-wear outfit ideas. 

Whether you go for a glamorous stiletto heel or a chic suede riding boot, knee-high boots are incredibly versatile. From teaming with the best midi dresses to smartening up the best leggings, they are worthy of a spot in your capsule wardrobe.

There are elegant styles that will work for evening wear and sharpen up daytime looks. More casually, the rubberized Wellington boot has been a favorite with the fashion set for a while and will give any look a cool, grungy edge (and they will come in handy during any unexpected showers too—alongside the best waterproof jackets).

How to style knee-high boots—outfit ideas from our fashion experts

Give your knee-high boots a refresh with these simple and stylish outfit ideas.

1. Knee-high Boots And Jeans

How to style knee-high boots with jeans street style

(Image credit: Getty)

What you need…

This classic combo is a fail-safe option for weekend dressing. Although most people will veer towards skinny styles as they are easier to tuck into boots, for a new season refresh try a slightly looser straight fit or mom jean instead. Thethe looser fit around the thigh will add a retro spin. 

A styling tip...

Pull the look together and nail the smart-casual aesthetic by adding your best blazer and a sleek shirt.

Our fashion editor recommends…

2. Knee-high Boots And Leggings

how to style knee-high boots with leggings street style

(Image credit: Getty)

What you need…

  • Flat boots
  • Leggings
  • Hoodie

You almost certainly consider leggings to be an essential part of your best loungewear looks, but, when styled right, they can work outside the house too - and the knee-high boot plays a key role. Boots will make leggings look smarter and more put together, and leggings will easily slip inside your boots. 

A styling tip…

Offset the tight fit of leggings with an oversized hoodie or sweater.

Our fashion editor recommends…

3. Knee-high Boots And Long Dress

how to style knee-high boots with a midi dress street style

(Image credit: Getty)

What you need…

  • Heeled boots
  • Printed midi dress
  • Belt

For a flawless look that will work for your workplace, a midi dress and knee-high boots make a great combo. Longer boots combined with longer skirts are always a classy option. 

A styling tip…

Add a belt to define your waist and streamline your silhouette. 

Our fashion editor recommends…

4. Knee-high Boots And Mini Dress

how to style knee-high boots with mini dresses street style

(Image credit: Getty)

What you need…

  • Pointed boots
  • 90s inspired mini dress
  • Statement blouse

Short hemlines are one of the top fashion trends for 2022, but if you find the idea a little daunting, you can offset a shorter style with longer boots. Go for pointed toes to help lengthen legs or stompy flat boots for a 90s vibe. Add tights for extra warmth during the colder months.

A styling tip…

Make summer mini dresses wearable all year round by layering them over a flouncy blouse or a cozy roll neck.

Our fashion editor recommends…

5. Knee-high Boots And Skirt

how to style knee high boots with skirts street style

(Image credit: Getty)

What you need…

Much like a floaty frock, knee-high boots will take a simple skirt to new heights—literally. Flat boots can feel a bit frumpy with this getup, especially if the skirt is a midi-length so look for heels. Let the boots be the main event, perhaps using prints, textures or eye-catching shades, and keep the rest of your outfit low key.

A styling tip…

Boots are a great item to wear with pleated skirts and with flared skirts. Add your best cashmere sweater for a daytime look.

Our fashion editor recommends…

6. Knee-high Boots And Trench Coat

how to style knee-high boots with a trench coat street style

(Image credit: Getty)

What you need…

  • Slouchy boots
  • Trench coat
  • Statement accessory

The trench coat is a longstanding fashion essential with a timeless, elegant appeal and a shape that compliments knee-high boots. Whether you choose to wear your coat open (and show off a killer outfit underneath) or fastened up, the trench and boot combination is a classic route to daytime sophistication. 

A styling tip…

For a fashion-forward look, stick to a simple color palette and team a beige trench with cream boots and gold jewellery.

Our fashion editor recommends…

Charlie is the Acting Deputy Fashion Editor across multiple women’s magazines and also a freelance fashion, beauty and lifestyle editor. 


She bagged her first magazine job in 2009 and has previously written for titles including Woman & Home, Closer and Dare. Over the years Charlie has embraced anything that was thrown at her from styling celebrities to testing out the best jeans on the high street to writing about must-have beauty buys. 


With a weakness for a printed midi dress, Charlie is on a mission to shop more sustainably and loves finding new ethical brands and second-hand buys.