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

Learning how to style knee-high boots will really open up your wardrobe choices. Here are 6 knee high boot outfit ideas

three women showing how to style knee-high boots
(Image credit: Getty Images)

With winter in full swing, learning how to style knee-high boots in a fresh and contemporary way will open up a host of outfit possibilities. A practical and versatile buy, we show you six knee-high boot outfit ideas to get you started.

When it comes to boot trends, no silhouette is as enduring as the best knee-high boots. While the style once again made an appearance on the runways, the truth is, as winter rolls around, a pair of knee-high boots will become a lynchpin to your winter looks. Neutral coloring is the wisest choice, as these boots will go with anything, with a host of bold colors very much 'in' this season, a bright pair of boots will instantly lift any monochromatic looks this winter. When it comes to fabrication, leather is the hardest-wearing material, although you could also look for vegan alternatives if you don't want animal products. 

Knee-high boots are incredibly versatile, whether you go for a glamorous stiletto heel, a practical flat, or a directional block heel, this is one winter shoe you can rely on. And when it comes to how to style knee-high boots, the options are endless. From teaming with dresses of all lengths to adding polish to legging outfits, there is nothing that a pair of knee-high boots can't help to elevate. Like with many of the best outfits, balancing proportions has a lot to do with how to style knee-high boots well. Here are six outfit ideas to get you started. 

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

One of the best winter boots around, knee-high boots are a true capsule wardrobe investment piece. Classic styles can go with multiple outfits and if well looked after can be integrated into your winter outfit ideas for many years to come. Here are six examples of how to style knee-high boots effortlessly, every, single, day. 

1. How to style knee-high boots with 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 jeans as they are easier to tuck into boots, for a new season refresh try a slightly more relaxed, straight-leg jean or directional mom jeans to switch up your look. The looser fit around the thigh will add a retro spin. 

A styling tip...

For a smart casual outfit idea, that feels immediately polished and put together, simply slip on your best blazer and a sleek shirt, with a pair of jeans and knee-high boots. A streamlined look, it will highlight your silhouette and feel smarter than wearing the best white trainers.

Our fashion editor recommends…

2. How to style knee-high boots with leggings

how to style knee-high boots with leggings street style

(Image credit: Getty)

What you need…

  • Flat boots
  • Leggings
  • Hoodie

When it comes to leggings outfits, many think that slipping into a pair of leggings is similar to your best loungewear, but styled right, leggings work brilliantly out the house too, and as their popularity has grown, so to has the choice of colorways and fabrications, meaning this is an item to play with this season. Knee-high boots are a great choice of shoes to wear with leggings too, instantly make leggings look smarter and more put together. Similarly to jeans, leggings will easily slip inside your boots, giving you a streamlined look that lengthens your silhouette in the process.

A styling tip…

Offset the tight fit of leggings with an oversized hoodie or sweater to help balance proportions.

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, the best midi dresses and knee-high boots make a great combo, as styling knee-high boots with a longer skirt length is always a chic option. When it comes to silhouette, you can wear knee-high boots with any shape of midi dress, from a slink pencil shape to a full A-line.

A styling tip…

Add a belt to define your waist, as this will create a nipped in, hourglass silhouette, especially with A-Line dresses that then flare out. 

Our fashion editor recommends…

4. How to style knee-high boots and a 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 2022, but if you find the idea a that much leg on show little daunting, you can offset a shorter style with longer boots. And while over the knee boots are big news this winter, a pair of knee-high boots will work too and are more versatile in the long run. Opt for pointed toes to help lengthen legs or stompy flat boots to pay homage to the '90s fashion trends around right now. Add tights or the best cashmere socks for extra warmth during the colder months.

A styling tip…

Make mini dresses wearable all year round by layering them over a flouncy blouse or a cozy roll neck for added warmth on your torso. Tights and boots will keep your legs warm.

Our fashion editor recommends…

5. How to style knee-high boots with a skirt

how to style knee high boots with skirts street style

(Image credit: Getty)

What you need…

Similarly to how to style knee-high boots with a dress, the humble knee-high will also take any skirt to new style heights. Any heel height works with this silhouette, although a flat boot will automatically feel a little more relaxed than heels and ideal for wet and cold days on the go. For a more dressed up feel, look for a more slender heel, over trend-leg chunky soles to add a softness to your look.

When it comes to skirt lengths and styles, anything works with boots, from minis to midi hemlines, knee-high boots will even look great as part of a long skirt outfit - especially if the skirt has a slit. 

A styling tip…

Boots are a great item to wear with pleated skirts and with flared skirts, just 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 - and almost any outfit. Whether you choose to wear your coat open (and show off a killer outfit underneath) or fastened up, a trench coat and boot combination is a classic route to daytime sophistication. 

A styling tip…

For a fashion-forward look, stick to a neutral color palette and team a beige trench with classic boots and gold jewelry.

Our fashion editor recommends…

Charlie is the Deputy Fashion Editor at Future plc across multiple women’s magazines including Woman & Home, Woman and Woman's Own.


She bagged her first magazine job in 2009 and has previously written for titles including Stylist, 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.

With contributions from