How to style knee-high boots: 6 outfit ideas to wear all year round (2024)

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

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(Image credit: Getty)

What you need…

  • Tan boots
  • Your best jeans
  • Blazer

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…

Ted Baker Shannie Heeled Boots

RRP: $325 / £225 | Tan boots are as versatile as black, but add lightness to any look, making them ideal for transitional outfits in spring and fall. The chunky heel adds heights without compromising on stability and we love the rounded toe.

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Everlane The 90s Cheeky Jean

RRP: $108 / £105 | These retro inspired jeans are a bestseller, largely thanks to their bum-boosting abilities. They sit high on the waist and have a relaxed, straight leg cut, that finishes just above the ankle bone. Available in eight different washes.

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Mango Houndstooth Blazer

RRP: $99.99 / £59.99 | A checked blazer adds a fashion-forward twist to any look. The green and brown houndstooth featured here adds a much welcome pop of color to this classic look, while the oversized fit plays perfectly into this season's trends.

2. How to style knee-high boots with leggings

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(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…

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

H&M Knee-high boots

RRP: $74.99 / £39.99 | Switch up classic black boots for a lighter shade of tan, as they're just as versatile. With a soft satin lining for added comfort, these chunky, lug sole boots, give a nod to the fall winter shoe trends 2022 that were all about stompy boots.

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Uniqlo Heattech Cotton Leggings

RRP: $24.90 / £19.99 | Some of the warmest leggings, this pair utilizes Uniqlo's HeatTech technology for a cozy but comfortable fit. In classic black, this pair of cotton leggings will literally go with any outfit and can be worn with tunics and long knits.

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Cos Oversized Scuba Hoodie

RRP: $115 / £69 | Made from scuba fabric for a modern touch, this stylish hoodie has sustainable credentials. The oversized fit is perfect for teaming with leggings, balancing out the fitted leg, while the soft pink hue adds a feminine touch to a sporty style.

3. Knee-high Boots And Long Dress

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(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…

How to style knee-high boots: 6 outfit ideas to wear all year round (10)

Dear Frances Porto Boot

RRP: $850 / £660 | When it comes to how to style knee-high boots, this pair add instant polish, with their super sleek design smartening up any look. Made from buttery soft Italian leather, the low-block heel makes them wearable around the clock.

How to style knee-high boots: 6 outfit ideas to wear all year round (11)

& Other Stories Printed Dress

RRP: $199 / £95 | This throw-on and go frock pulls out all the stops with its tie detail neckline, feminine floral print and elegant shirt shape silhouette for a timeless wear. Teamed with knee-high boots it gives off a gorgeous '70s-inspired boho style.

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RRP: $95 / £58 | This simple belt will add a dose of glamour to your outfit. Made from leather with a gold-tone metal buckle, we love the horseshoe shape for added interest. This slim belt is ideal for cinching in dresses, or slipped on over a cozy knit.

4. How to style knee-high boots and a mini dress

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(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…

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Dune London Spice Knee-High Boots

RRP: $270 / £195 | Some of the best black boots, these sleek boots have a smart stiletto heel and reptile-effect leather. The pointed toe helps to elongate your legs, which will look endless when these are paired with opaque tights or leggings slipped inside.

How to style knee-high boots: 6 outfit ideas to wear all year round (15)

Zara Belted Mini Dress

RRP: $59.99 / £45.99 | The perfect day to night dress. This fit and flare shape is universally flattering, nipping in waistlines and skimming thighs for a leg lengthening finish. The higher neckline keeps it chic, whilst the belted waist adds extra detail.

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Oliver Bonas Hairband

RRP: $43 / £29.50 | Statement hairbands are great accessory to style with knee high boots if you're looking to elevate your boots for a more evening look. The embellished design adds glitz and glamour - ideal for slipping on for the party season.

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

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(Image credit: Getty)

What you need…

  • Smart boots
  • Swishy skirt
  • Your best t-shirt

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…

How to style knee-high boots: 6 outfit ideas to wear all year round (18)

Zara Heeled Leather Boots

RRP: $169 / £119 | Cream boots do make quite a statement, but this chic pair is ideal for adding a vintage twist to any skirt outfit. To style these knee-high boots, look for complimentary neutrals that will work well with these brighter, knee-high boots.

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Whistles Dash Dot Belted Midi Skirt

RRP: $239 / £119 | This pleated midi skirt could be your new wardrobe staple. The built-in belt offers a flattering finish, allowing you to highlight your waist and balance the wider A-line finish. Complete the look with a fitted, tucked in, white tee.

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J Crew Slim Perfect Fit T-Shirt

RRP: $36.50 / £41 | It’s worth paying a bit more for essentials with extra longevity, and this simple white tee is expertly made. While a white t-shirt will need to eventually be replaced, looking for fitted, breathable styles that retain their shape is a good investment.

6. Knee-high Boots And Trench Coat

How to style knee-high boots: 6 outfit ideas to wear all year round (21)

(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…

How to style knee-high boots: 6 outfit ideas to wear all year round (22)

Manolo Blahnik Calassohi 90 Knee-high Boots

RRP: £1,295 / £995 | The slouchy fit gives these boots a boho vibe while the pointed toe keeps them looking elegant. The suede fabrication adds an extra layer of glam and these boots could easily be styled with sequins for a party-ready evening outfit.

How to style knee-high boots: 6 outfit ideas to wear all year round (23)

Ted Baker Robbii Belted Beige Trench Coat

RRP: $475 / £275 | A classic with a twist, this trench from Ted Baker 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.

How to style knee-high boots: 6 outfit ideas to wear all year round (24)

Oliver Bonas Emilia Chevron Color Blocked Bag

RRP: $67 / £46 | This cute camera-style crossbody is roomy enough for all of your essentials and the zipper fastening ensures they stay safe too. The chevron stripe is a timeless design, while the colorful sections make this an all-year wear.

How to style knee-high boots: 6 outfit ideas to wear all year round (2024)

FAQs

How do you wear over-the-knee boots over 40? ›

Knee-high-boots look best with wide midi skirts that cover them completely, skinny jeans, m riding pants. Style skirts with slim or tight sweaters. It is better to style a chunky sweater or tight or tailored shirts with sporty blazers and riding pants.

How do I make my knee-high boots look classy? ›

Since this is a pretty simple outfit, try dressing it up by adding some silver hoop earrings or some bracelets.
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Apr 14, 2024

What to pair with knee-high boots? ›

Knee high boots can be styled with short, knee length or even midi skirts and dresses. This gives your outfit a mix of feminine and modern touches and the boots help take your favourite clothing pieces through every season. During the colder months you can wear a pair of tights or leggings under your boots.

How to wear over-the-knee boots in 2024? ›

Knee high boots are surprisingly so versatile! I felt like all of these outfits I've shared give off different vibes. One of my personal favorites was what I wore for Thanksgiving. But that's the beauty of knee high boots: Pair them with jeans, dresses, skirts, or leggings – there's an outfit out there for everyone.

How to wear knee-high boots this season? ›

Embrace the trend of oversized pieces to create a fashion-forward look that perfectly compliments your knee high boots this spring. Opt for an oversized jumper or shirt paired with fitted bottoms like skinny jeans or leggings to balance out the volume.

Do people wear knee-high boots in the summer? ›

The versatility of a boot can't be beaten, whether it's a combat boot for an edgier look or a pair of knee-highs with a skirt for a more delicate ensemble, there are endless amounts of outfit combinations on how to wear tall boots in the summer.

Can a 50 year old woman wear over-the-knee boots? ›

If you have proportionally longer legs and lean limbs, you can wear this look well … IF you like the look,” says Rebecca. “I suggest never wearing a trend just because it's a trend. I've seen 20-year-olds look great in over-the-knee boots and some 50-year-olds who look way better than the younger ones.

Who should not wear knee-high boots? ›

For example, a shorter person shouldn't wear a knee-high boot that hits them too high, or someone with thin legs shouldn't pick a boot in which their calves are swimming (a tapered boot or a boot with a zipper or elastic could be ideal in this case), Read noted.

Do knee-high boots look good with jeans? ›

Knee high boots and jeans are a timeless styling combination. Day or night, this pairing is reliable, timelessly chic, and comfortable.

Are knee-high boots flattering? ›

Knee-high boots look fantastic with skirts, dresses, leggings, and tucked-in jeans. They are particularly flattering for those with longer legs. If you have shorter legs, consider wearing knee-high boots with heels to add height and elongate your silhouette.

Can I wear knee-high boots with dresses? ›

Knee high boots are statement makers. Whether styled in spring or winter or with jeans or a dress, they offer a sleek, put-together look that will effortlessly take you from the office to an evening get together in style.

What trousers to wear with knee-high boots? ›

Embrace the casual-cool vibe with a classic denim outfit paired with your favourite knee high boots. Opt for a pair of distressed jeans for that effortlessly chic look. Whether you choose to tuck them into your boots for a sleek appearance or cuff them up slightly for a more relaxed feel, you can't go wrong.

Should knee-high boots be tight or loose? ›

How should knee high boots fit? With this style you want it to fit as tightly but as comfortably to your leg as possible. This ensures that they don't slip down when you are walking or dancing the night away.

Do you wear stockings with knee-high boots? ›

Can you wear knee-high boots without tights? Yes, you can wear socks or knee highs while tucking your jeans in your boots, wearing skinny jeans or wearing leggings. The only time I wear tights or hosiery, other than knee highs, while wearing knee high boots is when I'm wearing a skirt or dress.

How do you casually wear knee-high boots? ›

Knee-high boots look great worn with your favourite pair of skinny jeans. Baggier styles of jean don't work quite as well, so stick to skinny if you can and tuck them in to show off the full length of your boots. Throw on a cosy jumper and you have a quick and easy winter look that is so simple yet so elegant.

What time of year can you wear knee-high boots? ›

The short answer is YES! And by boots I mean booties, shooties, mid-calf boots and knee-high boots. When to stop wearing boots comes up on our forum every year, and each time I suggest the same thing: weather permitting and if you're comfortable with the coverage, wear any style of boot year round.

How to style over knee boots? ›

I think over the knee boots look best with skirts that are a little shorter, so there's a gap of leg between the boot and the shoe. But if it's winter and you need your legs covered, wear a midi or maxi skirt and wear your boots underneath.

Can you wear knee-high boots in the summertime? ›

CAN YOU WEAR BOOTS IN THE SUMMER? Yes. Boots can easily refresh your summer wardrobe when worn well. The key is to pair your shoes with light layers that won't trap heat.

What length skirt to wear with knee-high boots? ›

Style with… a midi skirt

When it's not quite chilly enough for tights but bare legs feel too summery, knee-high boots are the chic solution. Unless you're tall, you may feel that a flat boot and a midi skirt makes for a slightly frumpy formula, so pick a style with a heel.

Are knee-high boots still in fashion in 2024? ›

Boots never go out of style, and in 2024, they will continue to be a key wardrobe staple for versatile and fashionable looks. As we move into the new year, there are fresh outfit ideas for styling our favorite boot silhouettes. From everyday ankle boots to daring knee-highs, boots elevate any cold-weather ensemble.

Can you wear knee-high boots over jeans? ›

Definitely! Best with skinny or slim-straight denim styles, so less fabric bunching around the knees.

Are tall boots with skinny jeans still in style? ›

Don't save tall boots for skinnies.

While yes, skinny jeans work well to tuck in to a boot, a slightly less tight jean looks fantastic too. That's a newer way to wear it, so you might not be ready yet, but be aware, it's on the horizon.

Are people still wearing knee-high boots? ›

As any savvy shopper knows, fashion is cyclical, and if you hang on to your beloved pieces long enough, they'll eventually come back into style. This is definitely true for classic knee-high boots, which are reentering the fashion circuit in a big way.

What age can you wear over-the-knee boots? ›

Women of any age can wear over-the-knee boots and look more elegant and sophisticated. These classic boots have been in style for a long time, even for women over age 40 or more.

Can you still wear over-the-knee boots? ›

Rest assured, these statement-making boots aren't just a winter fashion trend. Whether you're aiming to elevate a casual look or add a touch of edginess on a night out, over-the-knee boots are a go-to choice.

Is it okay to wear over-the-knee boots with jeans? ›

Since these boots are so fitted all the way up, they're best with a fitted pair of jeans, not looser. Pair them with skinny jeans for a sleek look. You can do lighter wash, mid wash, or darker wash blue, or white or gray or black. Anything works well, regardless of what color of boot you have.

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