As we turn into the cooler season, learning how to style knee-high boots is an essential styling move that can open up a host of outfit possibilities. The best knee-high boots are a practical and versatile staple, so we've rounded up 5 failproof outfit formulas to see you through the season.
If you've followed the autumn/winter shoe trends 2025, you'll know that 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 the cooler season rolls around, a pair of knee-high boots will become a linchpin in your autumn capsule wardrobe. Dark neutrals are the wisest colour choice, as these boots will go with anything, and when it comes to choosing materials, leather is the hardest-wearing material, although you could also look for vegan alternatives if you don't want animal products.
Plus, if you're hunting for autumn outfit ideas, 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 cold-weather 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 leggings 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 five outfit ideas to get you started.
How to style knee-high boots – outfit ideas from our fashion experts
1. How to style knee-high boots with jeans
This classic combo is a fail-safe option for weekend dressing. We'd recommend opting for skinny jeans as they are the easiest to tuck into boots. You could also try a slightly more relaxed, straight-leg jean or directional wide-leg jeans to switch up your look. The loose fit around the thigh will add a retro spin.
For a smart casual outfit idea that feels immediately polished and put together, simply slip on a tailored 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.
Tan boots are as versatile as black, but add lightness to any look, making them ideal for transitional outfits in autumn. The chunky heel adds height without compromising on stability, and we love the rounded toe.
These skinny jeans have a sculpting silhouette that will fit and flatter. They sit high on the waist and have a cut that finishes just above the ankle bone. Available in six different washes.
A checked blazer adds a fashion-forward twist to any look. The brown check featured here ties into the British heritage print trend, while the relaxed fit feels effortlessly chic.
2. How to style knee-high boots with leggings
When it comes to comfort, leggings paired with knee-high boots are always a winner. Styled right, leggings work brilliantly out of the house too, take cues from Claudia Winkleman's Traitor's outfits. Similar to skinny or straight jeans, leggings will easily slip inside your boots, giving you a streamlined look that lengthens your silhouette in the process. Offset the tight fit of leggings with an oversized blazer or chunky knitwear to help balance proportions.
These chunky heel knee-high boots will pair with almost anything from your wardrobe. The chunky small heel will be a lot more comfortable than stiletto styles, meaning they can be worn all day long.
Some of the warmest leggings to see you through the season in style. This pair utilises thermal technology for a cosy but comfortable fit. In classic black, this pair of leggings will literally go with any outfit.
This luxe jumper is made from a blend of Italian merino wool and cashmere that will keep you warm in the cooler season. The relaxed fit is perfect for teaming with leggings, balancing out the fitted leg.
3. Knee-high Boots And Long Dress
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.
When it comes to how to style knee-high boots, this pair adds instant polish, with its super sleek design smartening up any look. Made from soft leather, the low-block heel makes them wearable around the clock.
This throw-on and go frock pulls out all the stops with detailed, feminine floral print and elegant tie-waist. Teamed with knee-high boots and a sleek, tailored blazer for a look that works AM to PM.
This sleek, tailored blazer will add a touch of glamour to your everyday attire. Crafted from a smooth stretch fabric, this black blazer is soft to the touch. Layer over feminine dresses, or pair with the matching trousers.
4. How to style knee-high boots with a skirt
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 is ideal for wet and cold days on the go. For a more dressed-up feel, look for a more slender heel, over-trendy leg chunky soles to add softness to your look.
When it comes to skirt lengths and styles, anything works with boots, from minis to midi hemlines, and knee-high boots will even look great as part of a long skirt outfit, especially if the skirt has a slit. Knee-high boots are a great item if you're wondering how to style a satin skirt for work; just add your best t-shirt for a daytime look.
Slender heeled boots do make quite a statement, and this brown pair is ideal for adding an elegant twist to any skirt outfit. To style these knee-high boots, look for complementary dark autumn colours such as burgundy or mocha.
This satin skirt could be your new wardrobe go-to. The sleek satin material offers a flattering finish. Complete the look with a fitted, tucked-in, white t-shirt or a lightweight jumper.
It’s worth paying a bit more for essentials because a white t-shirt is something you will reach for time and time again. With a great fit, versatile crew neckline and breathable fabrication, this one is worth the investment.
5. Knee-high Boots And Trench Coat
Shopping for one of the best trench coats this time of year is a longstanding fashion tradition. With a timeless appeal and a shape that complements knee-high boots - and almost any outfit, a trench coat never goes out of fashion. Whether you choose to wear your coat open (and show off a killer outfit underneath) or fasten it up, a trench coat and boot combination is a classic route to daytime sophistication. For a fashion-forward look, opt for burgundy boots and team them with a classic beige trench.
The pointed toe gives these boots a boho vibe while the heel keeps them looking elegant. The deep burgundy hue adds an extra layer of glam. These boots could easily be styled with sequins for a party-ready evening outfit.
A classic with a twist, this trench from Nobody's Child is the perfect transitional cover-up. When it comes to how to style knee-high boots, the trench coat adds a layer of tailoring to your look, elevating your boots to boardroom-ready.
This elevated crossbody is roomy enough for all of your essentials, and the added pockets ensure your belongings stay safe, too. The rich chocolate brown aligns with the autumn/winter fashion trends 2025.
FAQs
Are knee-high boots still fashionable?
Knee-high boots are still very much in fashion, and they have played a consistent part in this year's shoe trends, spotted on several designer runways, from Burberry to Chloe. This season, think supple leathers in dark autumnal neutrals such as chocolate brown, deep burgundy, or simply black. Pointed-toe silhouettes are also in favour, giving off a boho-inspired feel.
What not to wear with knee-high boots?
In short, you can wear almost anything with knee-high boots. While many people gravitate towards skinny or straight leg trouser silhouettes, don't feel limited to that rule. You can absolutely wear wide-leg silhouettes if the boots fit comfortably underneath, creating a stylish layered look.
