Wear knee high boots

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How to Wear Knee High Boots

While footwear trends come and go, the popularity of knee-high boots has stood the test of time. Of course, it’s easy to understand why. These classic boots certainly have a lot to offer women. As well as providing warmth in the colder months, these shoes are also seriously chic and surprisingly versatile. Perfect for work, the weekend, nights out and beyond, knee-high boots can look fantastic with a variety of outfits. All you need to know is how to style them right, which is where we step in. Here’s our guide on how to wear knee-high boots for a gorgeous look.

Knee High Boot Styles

Black Knee High Boots

You can’t go wrong with black boots in winter, and even more so, black knee high boots. These are great staples to have in your wardrobe, ensuring that they’ll match any outfit you decide on. If you’re feeling adventurous, opt for a patent black boot or if you’re new to the trend, try black suede for effortless style. The great thing with black boots is that you can take them from daytime to nighttime, meaning you’re ready for whatever is thrown your way.

Shop the Look

Brown Knee High Boots

The brown knee high boots are extremely versatile – although they’re mainly associated with winter, don’t be so quick to put them on the top shelf when the weather warms up. For the colder months, wear your brown knee high boots with jeans for a casual look. Dress them up with a winter coat in a matching neutral tone. As it heats up, opt for a floral dress or denim mini skirt to rock the look all year round.

Suede Knee High Boots

You can never go wrong with a suede boot, let alone a suede knee high boot. The must-have shoe for any winter outfit, you can style it in endless ways that cater to different occasions or style preference. Wear them with a knitted dress for a casual vibe, or edge them up with a black mini skirt. A pop of bare skin goes well with suede, just make sure to get the right tone so it won’t wash you out.

Leather Knee High Boots

There are so many different ways to play with leathers to mix up your outfit. If you’re wanting to make a statement with your outfit, ditch the standard black option and try boots in coloured or textured leathers. Alternatively, opt for unique stitching or lace-up details in knee high leather boots to take your outfit to the next level.

Flat Knee High Boots

Heels may not be everyone’s idea of a good time, and quite frankly, they’re painful. Luckily, the knee high boot has a statement of its own, making a heel optional. Play with different textures to make a statement, such as snakeskin or leather. Pair them with jeans, a white tee and a leather jacket for a chic, relaxed outfit. Alternatively, throw on a knitted khaki dress with grey suede knee highs, and you’re ready.

Heeled Knee High Boots

There are some hot knee high boot styles out there at the moment, with metallic details, red patent leather and bright colours making waves in the industry. This move away from blacks and greys toward colour means a chance for playful expression in your outfit, with fun boots to match. Different heel heights and shapes for women means you can still ooze sophistication without hurting your feet in a high heel. Even better, you’re still playing with the traditional winter boot. Opt for a chunky heel for a modern look or a stiletto for a more glamorous vibe.

Knee High Boot Outfits

Knee High Boots with Jeans

Wearing your favourite knee highs with jeans is so simple yet elegant, creating the “I just threw this on” look. So versatile, you can pair any jeans with your boots, whether it’s your favourite denim or other tones that you love. To keep it all flowing, try opting for skinny jeans as the baggier the pant, the less shape it will give your figure. To elongate the body, try tucking your shirt or jumper in at the front, and the slim jean will ensure you’re not lost in the fabric.

Knee High Boots with a Dress

Pairing knee high boots with a dress creates the ultimate feminine outfit. Stylish and sophisticated, you can easily throw on a dress with your boots and still look well put together. For a sexy modern outfit, try a mini dress, with a flash of leg giving off the most stylish and on-trend look. The wide range of knee high boot styles allows for you to make a statement of your own, whether it’s the lace-up trend or simply a burgundy leather, meaning you can throw on a simple black dress and still stand out.

Knee High Boots with a Skirt

The different lengths of skirts make it so much fun mixing up the different outfit you’re going for. Again, try a mini skirt with a bare leg to break up the outfit, or pair your skirt with tights for the ultimate winter look. It doesn’t matter what length of skirt you decide on – a midi or maxi skirt also works, as the boot will pop underneath. If you’re finding yourself playing it a bit safe, why not try a leather skirt, giving your outfit a hint of biker style – you will be seriously on-trend.

Knee High Boots with Leggings

When chosen and worn right, leggings can be an ideal addition to your wardrobe. You can still look fashionable and well-dressed while being comfortable at the same time. Instead of opting for blacks, try cream leggings with beige suede knee high boots, teamed with a long grey knitted jumper. When layering over the leggings, the length in the back will ensure extra comfort and style.


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Need a way to make your wardrobe work harder? Let us introduce you to your new saviour: the knee high boot. This shoe has had a renaissance in recent years, going from standard staple to statement-making.

Fashion editors everywhere are channelling a demure, more-is-more approach, swapping skin for long hemlines and layers. We know what you’re thinking: not another trend to invest in. But, don’t worry, luckily everything you need to look chic this season is probably already lurking in your wardrobe – all you need to do, is add knee high boots.

So don’t put away the floaty midi dresses and skirts you wore all summer long just yet, they now feel super current layered over a pair of knee high boots. The best bit is, you no longer need tights to keep warm. (But even if you had a pair of ski thermals underneath that billowy number, no one would be able to tell – how liberating.)

And let’s not forget, this shoe is comfortable too. Whether flat, kitten or block heel, the overall surface area leads to more stability for your feet. Which is why we think the style is appropriate for any occasion: work, parties, winter walks, you name it.

Don’t believe us? Keep scrolling to see how we style knee high boots in four different ways.

How to wear knee high boots to work

Wool Shift Midi Dress jigsaw-online.com £120.00


80-denier opaque tights




Emma Leather Knee Boot Hobbs hobbs.com £215.10


Ribbed fitted turtleneck jumper M&S Collection marksandspencer.com £25.00


Letty clasp shoulder bag




Knee highs are smart enough to wear to the office, especially when they’re in shiny glossed leather like Hobbs’ version. Inspired by the classic Chelsea boot, this pair is set on a comfortable block heel and spliced with an elastic panel (which is great for wide-fitting calves, by the way). Wear them with mini skirts and shirts, long sleeved midi dresses or Jigsaw’s ’60s-inspired shift – just underpin it with a roll-neck and opaque tights.

How to wear knee high boots on the weekend

Faux fur-trimmed wrap coat Jaeger jaeger.co.uk £199.00

Polka-dot print midi dress




Evershot leather knee high boots Boden boden.co.uk £147.00


Leather crescent hobo bag M&S Collection marksandspencer.com £89.00


Cashmere-blend ribbed turtleneck




This season, the ’70s are back, so you can experiment with autumnal colour palettes and always look on trend. Boden’s burgundy boots are made from croc-effect leather and have sturdy block heels which will see you through busy days of errands, but also take you on to smart dinners. Pair yours with H&M’s polka dot midi dress, which feels cosy layered over a roll-neck now, but will work with sandals or trainers come spring.

How to wear knee high boots in the winter

Bell borg-trim faux suede coat Boden boden.co.uk £198.00 Magic lift high waist skinny jeans M&S Collection marksandspencer.com £35.00 Lottie buckled leather knee high boots Crew Clothing crewclothing.co.uk £99.00 Cable-Knit turtleneck sweater GAP gap.co.uk £179.00 Long cuffed cashmere gloves HUSH hush-uk.com £50.00


If you need your knee highs to be even more practical, go for a classic riding style with a low heel. With its expansive elastic panel and buckled straps, Crew Clothing’s look way more expensive than they actually are. Wrap up in chunky jumpers, cosy outerwear and cashmere gloves on your next winter walk.

How to wear knee high boots in the evening

Marie leopar-devore midi dress Boden boden.co.uk £75.00 Anja Gold Plated Drop Earrings Oliver Bonas oliverbonas.com £29.50 Kitten heel stretch-suede knee high boots M&S Collection marksandspencer.com £39.50 Georgina sequin drawstring clutch bag Phase Eight phase-eight.com £49.00

Phase Eight

Belted wool-blend coat

& Other Stories




Knee high boots also work for parties, and are far more comfortable than vertiginous high heels. Made from stretch suedette that is guaranteed to stay put (no one likes saggy ankles), Marks & Spencer’s version have an elegant kitten heel and pointed toe. Wear them with an all black outfit for versatility, then add sparkles in the form of accessories.

Related StoryPhoto: Edward Berthelot/Getty Images

There are two kinds of people in this world: Those who love living in slip dresses and slide sandals all summer long, and those who don’t think you can really dress until the temperature dips below 60. If you’re in the latter camp, you get a little thrill when it’s time to dust off your chunky knits and leather jackets — and wear them with the real MVP of this season, over-the-knee boots.

What makes OTK boots so great? Well, tall boots will keep your legs warm when you don’t want to wear pants. And once it gets really cold, you can layer them over skinny jeans for that cozy my-pants-are-wearing-pants feeling. The only challenge is knowing how to style them, which is why we asked 11 stylish women to show us their favorite knee-high boots outfits. Read on for lots of inspiration, as well as suggestions for the best tall boots out there.

Nnenna Echem, Content Creator

Instagram: @nnennaechem
How she wears her boots: I love the ones from Liu Jo. They’re the perfect length, with an unusual heel — but they are, of course, a bit pricey. Mango and Zara usually have cool over-the-knee boots in a more reasonable price range. I often style them with long skirts and a coat, but they also work with slim jeans and a blazer for a more relaxed look.

Liu Jo Over-the-Knee BootsHigh Tip Boots

Stephanie Moreno, Fashion Director and Consultant

Photo: Courtesy of Stephanie Moreno

Instagram: @steph
How she wears her boots: Over-the-knee boots are a dream; they replace pants, they suck in imperfections while offering comfort, and they make me feel powerful. I wear them as a replacement to trousers with oversize tops and/or knits, under my printed dresses to bring some edge, or with Levis shorts to give them a longer life into fall. I think OTK boots should be as close to a second skin as possible, which is why I always rely on Chanel, Ann Demeulemeester, Saint Laurent, and Chloé to make the best versions.

Saint Laurent Tanger 105 Leather and Suede Over-the-Knee BootsPointed Thigh High Boots

Julia Kondratink, Blogger at Humidity is the Enemy

Instagram: @humidityistheenemy
How she wears her boots: Most of the pairs that I own are from Steve Madden because of their great prices, comfort levels, and quality. I have big calves so wearing boots over jeans is usually problematic for me. I usually style my OTK boots with skirts and dresses. My favorite pair that I own are burgundy velvet — the color is just so rich.

Natalia Slouch BootSteve Madden Brinkley Over the Knee Boot

Channing Hargrove, Fashion Writer at Refinery29

Photo: Courtesy of Channing Hargrove

Instagram: @chan_inthecity
How she wears her boots: I’m pretty petite so it took me a while to come around, but now I wear over-the-knee boots almost as tights or leggings under sweater dresses, midi skirts, and even miniskirts with chunky knits on top. The pair getting the most love in my closet right now is from Marc Fisher (they’re on sale now!). They’re substantial enough to keep my legs warm and fall into a cozy slouch after I’ve had them on for a bit.

Marc Fisher Ulana Marc Fisher Women’s Nella Over the Knee Boot

Hélène Heath, Fashion Writer and Social-Media Expert

Photo: Courtesy of Helene Heath

Instagram: @heleneisfor
How she wears her boots: There’s something intrinsically badass about over-the-knee boots — you just can’t help but feel a sense of power when you wear them. Here I am in a pair from the Altuzarra x Target collection, which I love because the heel height is sensible enough and they’ve got a timeless toe and heel shape. If I reach for these boots, my outfit has to be all about balance. Because they’re quite sexy and make a pretty bold statement, I always try to tip the scales with something more casual or masculine. This particular look involved a vintage blazer with an apropos ’80s power-suit vibe and made me feel like a boss.

Women’s Norina Pointed Toe Sock Boots

Anaa Saber, Creative at @oursecondskin and Contributing Editor at WhoWhatWear

Photo: Courtesy of Anaa Saber

Instagram: @oursecondskin
How she wears her boots: Over-the-knee boots are my footwear of choice for the days I have no clue what to wear. It’s the easiest hack to dress-up an outfit and add a little extra kick (pun intended). These boots from Georgian designer the Situationist are one of my favorites at the moment.

Rachel Comey Hawks Over-the-Knee Boot The Row Bourgeoisie Leather Boot

Nadia Aboulhosn, Model and Creator of by Nadia Aboulhosn

Photo: Courtesy of Nadia Aboulhosn

Instagram: @nadiaaboulhosn
How she wears her boots: I usually wear thigh-high boots with a cute pair of shorts or a minidress. I know it’s sort of a trend now to layer longer pieces of clothing over them, but I love showing that little bit of skin before my hips. A few of my favorite brands for over-the-knee boots are Missguided, Pretty Little Thing, and Aldo.

Snake Effect High-Leg Boots Qoidia

Camilla Ackley, Founding Editor of Into the Fold

Instagram: @camillaackley
How she wears her boots: I love OTK boots with a strong heel — something about them makes me feel like I’ve actually got my shit together, even if I definitely don’t that day. They are a power shoe, if ever there was one. I usually wear my suede pair with a wrap midi-dress for work. If I want to go full out for a party, I’ll pair them with a vintage black velvet minidress that my mum used to wear in the ’90s. It feels very Austin Powers and I’m here for it. Obviously Stuart Weitzman is the king of OTK boots, but & Other Stories always deliver strong options for a less hefty price tag.

Knee High Suede Boots The Tieland Boot

Sharee Burns, Fashion Blogger at Ro$es are Red and Freelance Stylist

Instagram: @___vixen
How she wears her boots: As a curvy woman, it can be hard for me to find cute over-the-knee boots. Luckily, a lot of popular online retailers are becoming “fit-inclusive,” with various styles of boots for women with different leg sizes. ASOS and Jeffrey Campbell are two of my favorites. I cannot live without these ASOS Design Kera pointed thigh-high boots. They make me feel so sexy. Plus, they’re comfortable. I wore them to an event one night with my boyfriend and all night I felt as if I was walking on air! They didn’t droop or fall down every time I moved. For the fall, I am excited to wear with skorts and turtlenecks for a Parisian vibe.

ASOS Design Kera Pointed Thigh-High Boots Jeffrey Campbell Final Slouch Over the Knee Boot

Noor ElkHaldi, Content Creator at @noore

Photo: Courtesy of Noor Elkhaldi

Instagram: @noore
How she wears her boots: I’m obsessed with white over-the-knee boots right now. Amina Muaddi’s Olivia 95 leather ones are the perfect pair, but Sam Edelman also does an amazing white OTK boot as well. A good pair of black OTK boots are an absolute staple in my FW wardrobe. I love these Kalda black patent leather boots — I think they would look so cool with a more feminine mini dress. I’m very into pairing a silk midi skirt and OTK boots at the moment. I just love the way the skirt moves and the boots seem endless underneath — it’s a very elevated layered look.

Amina Muaddi Olivia 95 Leather Over the Knee Boots Hutton Boot Kalda Black Eyja 80 Patent Leather Boots

Jessica Tran, Brand and Partnerships at Dagne Dover and Owner of Ghost Vintage

Photo: Courtesy of Jessica Tran

Instagram: @jessglistening
How she wears her boots: Stuart Weitzman makes reliably solid OTK boots — the Hilines are my go-to for winter nights out. But Mango makes trendy, more affordable alternatives. My favorite way of styling them? Always with a miniskirt and an oversize sweater or jacket and a beret.

Stuart Weitzman Hiline Over the Knee Boots $559 (was $798, now 30% off) Geometric Heel Boots

And Few More OTK Boots, in Case You’re Still Not Satisfied:

Thelma Over-the-Knee Boot S-Very Y-3 Kaiwa Tall Sneaker Boots

If you buy something through our links, New York may earn an affiliate commission.

Whether they’re leather or suede, flat-soled or with block heels, not only are thigh-high boots surprisingly wearable, but they’re well on their way to becoming cold-weather wardrobe staples. Pull them on over skinny jeans or leggings, style them with a midi skirt that falls below the top of the boot, or allow a sliver of skin (or tights, come winter frost!) to peek out between your boot and a short hemline. Just in time for fall, find out our favorite ways to wear thigh-high boots, below.

To make your Canadian tuxedo winter-ready, swap the open-toe heels for knee high-boots. Bonus points if they feature Western-inspired elements.

Edward Berthelot

& Other Stories Knee High Cowboy Boots

& Other Stories $299 Buy Now

Havva Texas Buckle Tall Boot

Havva $467.79 Buy Now

Intentionally Blank Inferno Patent Leather Boot

Need Supply $83.99 Buy Now

H&M Knee-high Boots

H&M $69.99 Buy Now

Snakeskin adds texture to any outfit—statement boots like these just make it that much easier.

COPENHAGEN, DENMARK – DECEMBER 12: Sonia Lyson is seen wearing turquoise knit, midi pleated skirt Samsoe Samsoe, Zara snake print boots, Chanel bag, red sunglasses Jimmy eyewear on December 12, 2018 in Copenhagen, Denmark. (Photo by Christian Vierig/Getty Images)Christian Vierig

Loeffler Randall Gia

Loeffler Randall $695 Buy Now

Dolce Vita Cormac Knee-High Boots

Anthropologie $260 Buy Now

Express Snakeskin Print Tall Western Boots

Express $98 Buy Now

RAYE Sinner Boot

Revolve $228 Buy Now

Breathe new life into that pencil skirt with suede boots. The contrasting fabrics will make it feel extra sophisticated.

LONDON, ENGLAND – FEBRUARY 20: Caroline Issa seen wearing Vetements in the streets of London on Day 4 of London Fashion Week February 2017 on February 20, 2017 in London, England. (Photo by Timur Emek/Getty Images)Timur Emek

UO Clara Knee-High Boot

Urban Outfitters $159 Buy Now

Bella Vita Karen II Boots

Macy’s $105 Buy Now

Labucq Babs Black Suede

Labucq $495 Buy Now

Sam Edelman Hai Tall Boots

Shopbop $120 Buy Now

A tall slouchy boot feels a little bit more laid-back than the average thigh-high. Style it with a slitted skirt so that it really stands out.

NEW YORK, NY – SEPTEMBER 10: Rachel Wang is seen attending Public School during New York Fashion Week wearing Isabel Marrant on September 10, 2017 in New York City. (Photo by Matthew Sperzel/Getty Images)Matthew Sperzel

Frye Women’s Lila Slouch Tall Boots

Macy’s $398 Buy Now

Coach Graham Slouchy Boot

Coach $225 Buy Now

Tory Burch Brooke Slouchy Boot

Tory Burch $219 Buy Now

Jeffrey Campbell Brutish Point Toe Boots

Shopbop $60 Buy Now

When in doubt, try monochromatic dressing. Start with a white boot, and match your layers and outerwear for an all-white look.

BERLIN, GERMANY – MAY 31: Tina Haase is seen wearing creme white Drykorn blazer and dress, Zara boots, Furla bag, Celine necklace, Gucci sunglasses on May 31, 2019 in Berlin, Germany. (Photo by Christian Vierig/Getty Images)Christian Vierig

Tony Bianco Jester Scrunch Boot

Revolve $161 Buy Now

Public Desire Mine White Slouch Knee Boots

ASOS $63 Buy Now

Stuart Weitzman Milla 60 Boot

Stuart Weitzman $795 Buy Now

Mango Leather High-Leg Boots

Mango $129.99 Buy Now

Knee-high boots have been a popular fashion trend almost consistently for over a decade. Few fashion trends have such staying power. Why have tall boots remained popular for so long? For the same reason that many fashion trends last and occasionally overstay their welcome – it’s a trend that is accessible to a variety of body types and budgets. Knee-high boots were practically a women’s fashion must-have from 2005-2015. But after a decade, the trend began to feel very tired. The style went from sleek heeled styles and classic riding boots to all sorts of fabrics covered with studs and buckles and plenty of stretch panels worn with a uniform of very skinny stretchy jeans and either a tunic sweater or a button-front shirt topped with a faux fur, quilted, or puffer vest. The trend had been so overdone there were memes made about it.

In 2017 I wrote a post about how knee-high boots were no longer in style and it angered a lot of people. The thing is, I never said to get rid of your knee-high boots. I suggested styling them in a fresh way or possibly retiring them for a while. If you didn’t own such boots already, to not buy them at that time. Well it’s almost 2020 and now is the time to take your knee-high boots out of storage and if you were wanting a pair, I recommend shopping now while there is plenty of selection. Recently I shared my picks for stylish wide-calf boots to give you some shopping inspiration. Below I share ways to stye knee-high boots for 2020 – the outfits are similar, but different and I share how the trends have changed.

How Knee High Boots Used to Be Styled

There were two ways that knee-high boots were styled in most of the 2000’s and 2010’s – either with short skirts and dresses having knees exposed, or slipped over skinny jeans and styled with lots of layers.

Some outfits from the archives showing how I styled knee-high boots before 2017: lots of layers on top with skinny jeans and often a very large bag.

The most popular way to wear knee-high boots during this era was what we now mock as “basic”. Knee-high boots styled with jeans or leggings and lots of layers. Think the cliché “Christian Girl Autumn” of blanket scarves, floppy hats, and steaming cups of pumpkin spice latte. Where I live, knee-high boots were quite popular with skinny jeans, plaid flannel shirts, and puffer or faux fur vests (I was known to rock this combination from time to time) which also inspired its own meme.

Looks from the archives where my kneecaps were shivering in the cold.

The other way knee-high boots were styled was with short skirts and dresses with knees and often a bit of thigh exposed. More often than not these looks were styled with bare legs. Hosiery went out of style for a bit during this time unless it was tights in a statement color, so boots were often put with looks that didn’t necessarily benefit from them just to stay warm.

How Knee High Boots are Styled Now

The way knee-high boots are stylish in 2019 is the way they were stylish before the late ‘00s and early teens. Think about how style icons across the decades wore such boots or would have worn such boots if they owned them. They are worn to keep one warm; they are tall enough to slip under a longer skirt to have no bare skin. They are worn slipped over pants and jeans when riding horses or being outdoors because they are fantastic wind protection and a fabric that can withstand a lot. The difference are the details.

Shop the Look: sweater | jeans | boots | earrings | watch | bag

At first glance, this look appears similar to how knee-high boots were styled a few years ago. But the difference is the details. The sweater is lightweight, not bulky and worn either tucked in or fitted and skimming the body. The jeans (which I own and love) are not skin-tight and have a higher rise which is a current trend. Having the boots and the jeans the same color elongates the leg and looks more luxe. Previously, the bag would have been chosen to match the color of the boots. Having the bag and accessories instead coordinate with the top makes the outfit airier and light while also giving a feeling of modern luxury.

Shop the Look: dress | boots | bag | bracelet | earrings

I’ve thought for over a decade that leopard print is a neutral; well this season has deemed snakeskin to also be a neutral. Not only that, it looks extra fresh and fashionable when mixed with other patterns. Previously, such boots would be styled with a short black dress and black tights, or black leggings and a black sweater to let the boots earn the spotlight. Make printed boots modern by letting them blend into the background and complement another pattern. Florals, paisleys, and graphic prints all look great with snakeskin and other subtly patterned knee-high boots. Since the pattern mixing is busy, keep the rest of your look simple a classic. High-shine gold jewelry that is classic with an edge, and a traditional-looking handbag in a color to pick up the dress print is a perfect addition and makes the print mixing purposeful.

Shop the Look: blazer | shirt | jeans | boots | earrings | necklace

Boots are still great slipped over skinny jeans, but to make the outfit modern, go classic. Instead of waterfall jackets, long sweater coats, puffer vests, and blanket scarves add some tailoring and an equestrian feel. Tweed, plaid, and wool blazers are popular this season and look so right with the riding boots that may already be residing in your closet. While a few years ago the trend would be to wear the blazer over a Breton striped tee, this season consider pairing it with something more traditional like a button-front shirt (I have this one and love how it doesn’t wrinkle, stretches, and looks fresh right out of the dryer while being comfy even under a blazer). Consider skinny jeans with a higher rise; button fly jeans have returned and offer an interesting outfit detail while also slimming the midsection.

Shop the Look: sweater | skirt | boots | bag | earrings | watch

The ’70s inspired look of a boot with a midi skirt is very on trend, and a cozy warm trend too! Whether it’s a wool a-line or a pleated silky fabric like the one featured above, this is a way to keep yourself completely covered while still looking dressy and work-appropriate. Continuing with a popular trend, I balanced the softness of the skirt with a thicker, shorter sweater. Half-tuck the sweater in front and leave the back loose to draw attention to the waist while still looking relaxed. I liked the monochromatic effect, but there is no need to do this; feel free to wear what colors you like or even have a patterned skirt. This look is best with a slim-fitting boot with at least a 1″ heel. I went with a beige suede which is a popular finish for knee-high boots this season, but honestly, any color, finish, and heel style can work with this concept.

The four looks above aren’t radically different from how we styled knee-high boots 5-10 years ago. The difference is the details – the fit, the silhouette, the subtle switch in patterns and cuts. The best way to make the knee-high boots in your closet feel modern is to ensure they fit well, look for ways that they can blend into your outfit instead of stealing the spotlight, and be sure they are in great condition. Take them to the cobbler to get reheeled, resoled, and a good polishing. Consider insoles for comfort (I personally love these and have them in several pairs of boots; they also come with a wool shearling version).

What Kind of Knee High Boots Should I Buy?

If you’re a grown-ass woman, you should be wearing grown-ass shoes. Go ahead and scrimp on jeans and t-shirts and denim jackets and casual dresses. But shoes are one place you should spend money. Not only do you deserve a comfortable shoe, but you’re too old to be wearing cheap leather alternatives and weird embellishments. Unless you are against leather, get leather. If it’s too expensive, wait. And make sure that leather is quality leather – thick enough that the shafts won’t slide down mid-day, a smooth finish that can handle being polished like grown-ass women do with their leather shoes, hardware and heels that would have looked at home in 1972 as well as 2022.

When Do I Need Knee High Boots with Heels?

Heels equal dressy in most situations. Adding a heel will read dressy and be a better pairing for skirts and in the workplace. A turtleneck sweater with jeans and flat boots – casual and comfy for a weekend of running errands. A turtleneck sweater with jeans and heeled boots – a chic look you can wear to brunch or to a creative workplace. A heeled boot adjusts the shape and appearance of one’s legs, making boots that are a bit shorter on the calf look more proportional.

That being said, heels are not necessary. A flat boot with a slim silhouette and almond-shaped toebox can still look quite polished. However, it’s even more imperative that the boot fits well. Cobblers can narrow boot shafts and some will even custom shape the shaft so it perfectly skims your leg from calf to ankle. Bulk-creating details like buckles above the ankle, elastic gussets, cuffs, and lacings will make a boot look less dressy and will also reduce its versatility.

What Color Knee-High Boot Should I Get?

What color you buy has everything to do with your existing closet and your goals for wearing the boots. A modern look right now is to have your boot match or be in the same color story as your pants, skirt, and/or hosiery. A snakeskin print chiffon dress with brown tights and brown boots. A teal sweater with black jeans and black boots. A camel blazer with cream jeans and brown boots. Gray suede boots with gray jeans and an ivory sweater. You get the idea. The low-contrast look is not only leg-lengthening but modern and definitely not 2015.

How Tall Should My Boot Be?

As I shared in my stylish wide-calf boots post, you should measure not only the calf width of your legs, but also the length from below the knee to the top of your heel. Everyone’s legs are different heights and you want to have boots at a stylish and comfortable height.

When you are petite, you may find knee-high boots bow out at the top like pirate boots, or they get caught in the back of your knee when walking or sitting. This means the boot is too tall. However, I think a boot just under the knee looks best on my short and wide-calf legs so I had a cobbler take my boots that looked like they belonged to Blackbeard and tailor them for a perfect fit. They have become the most-worn boots in my wardrobe.

When you are tall, you may find boots hit at an odd point on your calf muscle. Luckily, right now there is no specific height for boots so you can either rock that height if you like it, or look for a higher shaft. There are many styles of just over the knee boots with a lower back that look quite chic as traditional knee-high boots on taller legs.

Unless it fits your personal style, I don’t recommend right now buying half-height boots that hit mid- to low-calf muscle. That length is hard to wear not just because it can shorten and thicken the look of a leg, but because it’s harder to style. Knee-high boots are an investment and it makes sense to pick a style that is versatile and classic.

Do I Need Knee-High Boots in My Wardrobe?

Absolutely not. What is great about fashion right now is that it’s fluid. In the past, you would look dated if you had the wrong heel shape, the wrong pant leg opening, the wrong width of blazer lapel. Style now is about knowing yourself and expressing it through your wardrobe. No one needs knee-high boots, only purchase them if they fit your personal style.

The most important aspect for style these days is fit. If you do not have a tailor or cobbler, visit your city’s NextDoor or go to Yelp and look for one. Whether a dress or a boot is from Walmart or Saks Fifth Avenue, it will look more stylish if it fits you correctly. When items don’t fit right off the rack (or right out of the shoe box), it’s not because there is something wrong with you. Nobody, except the brand’s fit model, can wear clothes off the rack and have them look perfect. Celebrities and fashionistas – they look great not because they wear designer clothing but because they get everything, boots included, tailored to fit. Buy fewer items, buy slowly looking for the best quality and style you can find, and spend the money to get them tailored. You’ll end up with a smaller but more stylish and versatile wardrobe!

Shop the Post:

Allow me to introduce you to some dear old friends of mine: these boots. Every week in these photos, I wear something from my own wardrobe mixed with clothes that are in the shops now, and this week I’m wearing knee-high Mulberry boots that I wore and wore years ago, and that then languished in the bottom of my wardrobe for several winters, during which I wore ankle boots. Until last winter, when I sat catwalk-side, ankle-boot clad, watching knee-high boots in fashion shows and realised I wanted to wear them again, because… fashion.

So here they are. Except they look different, because the rest of my clothes are different. I’m not wearing skinny jeans these days, so I can’t wear my knee boots over the top of those, which was definitely a thing last time around. This time, the boots go under a loose, mid-length skirt. I know this because I saw it on the catwalks, like I said, but it’s taking a bit of getting used to now that I’m trying it out on me. This silhouette – a chunky heeled, sturdy boot disappearing under the hem of a skirt that swings loose below the knee – radiated effortless, laid-back nonchalance when I was watching it being worn by high-stepping 6ft-tall glamazons, but in the mirror, it looks a little… challenging, let’s say.

Challenging is good, though. Challenging is what new year is all about. This is the time of year to make some changes; maybe you will find a new job or go vegan. But for now, the out of office is on and there is brandy butter in the fridge that it would be silly to throw away, so in the meantime, boots are as good a place as any to start making changes. This is what I’m telling myself, anyway, while looking in the mirror and wondering why I look a bit like I’ve remembered, in the middle of a party, that I left my handbag in the car and have pulled on a pair of gardening boots to go and get it.

Worn under a loose skirt, my knee boots look less slick and more relaxed than they did when they were meeting the hem of a pencil skirt or had jeans tucked into them. But we’re getting used to each other, again. Should auld acquaintance be forgot, right? The new year starts here.

Hey, reader! While you’re here for boots inspiration, come see all the boots we’re shopping—in every height—inspired by the photos below: In any Glamour story featuring a shopping bag icon, you can instantly shop a selection of related products, curated by us. Check out our picks to your left on desktop and right on mobile. Happy shopping!

We’ll take boots in any height, from bootie to so-high-they’re-almost-pants. But of all the boot heights, knee-high boots are the ones we’re reaching for most often lately. Fashion is drawing heavily on the ’90s right now, and knee-high boots are meeting minidresses and high-slitted midi and maxiskirts right there. Street style can’t get enough of knee-high boots lately, so we picked our favorite looks and rounded up some major #OOTD inspiration below.

Hanna Lassen

This year’s coatdresses go perfectly with a pair of knee-high boots. (Bonus points if they’re metallic gold for a Friday night out.)

Claudio Lavenia

Not all of us live in cold winter climates: If you happen to be basking in the sun, consider adding a pair of knee-high boots to your favorite short-shorts. (If it is cold, a pair of black tights can bridge the gap.)

Claudio Lavenia

Knee-high boots, a street-grazing cape, and a sheer, embroidered blouse add drama to your favorite blue jeans.

Christian Vierig

Keeping your outfit monochromatic above the knee—here, a marigold top and miniskirt under a yellow-tan shearling coat—lets your excellent statement boots below the knee shine.

Edward Berthelot

A white top is anything but boring when worn with an array of luxe textures—here, snakeskin, velvet, and leather. So pulled together.

Daniel Zuchnik

Knee-length shorts look incredible when paired with a matching blazer and textured knee-high boots. Keep everything in the same color family, a nod to this year’s monochromatic trend, for an extra-fresh take.

Friday Fashion Fits: How to Wear Knee-High Boots with Anything

I guess we’re lucky that skirts are in because now they can replace skinny jeans for our knee-high boots outfits. A lot of people are looking for what to wear with knee-high boots for a night out, so we wanted to show you some knee-high boots outfit ideas and how to wear knee-high boots with anything…

How to wear knee-high boots with wide pants

With skinny jeans being ignored by so many people currently, a lot of us are confused as to how to wear wide pants or loose pants with knee-high boots. Culotte pants really cool with knee-high boots, especially if they’re a little shorter. You can also tuck your pants into your boots if you like, for more of statement, but very chic look.

How to wear knee-high boots with skirts

This is the most comfortable option for a lot of people and for good reason, it looks great. You can wear knee high boots with long skirts, short skits and denim skirts. They looks gorgeous in any case, depends on what skirts you have and what you feel more comfortable wearing. With a denim skirt, it would really nice if there’s a slit in the side so you can see more of the boot.

How to wear knee-high boots with shorts

I know what you’re thinking, shorts in winter? Yes, the right shorts are amazing in winter, especially with sheer tights underneath or you can buy wool shorts to keep you warm. You can get some wide shorts that fall right above the knees and wear them with knee high boots. It’s an outfit that will definitely start up conversations.

How to wear knee-high boots with dresses

Dresses are also a good comfortable choice. A short winter dress with white knee-high boots is a gorgeous ’60s look that I want for myself right now. With flowy dresses go for knee-high boots with heels, they will give length too your look and give the dress a nice flow.

How to wear knee-high boots with an oversized blazer

If you’re wondering how to wear knee high boots in the office, even though it’s not an easy look to pull off and of course it depends on where your work, you can definitely still make it work with pencil skirts, formal coats and oversized blazers.

Knee-high boots for petite women:

For petite girls, knee-high boots are your besties in winter because they give a lot of length and you can pull off the oversized baggy look as much as you want to, when you pair it with nice heeled knee-high boots. Ariana Grande wears them a lot and you can check out here how she perfects petite styling.

Scroll to see more knee-high boots outfit ideas…

Ask the Expert: Can I wear boots during the summer?

Q: I would like tips on wearing women’s boots/booties during the summer.

A: I’m all in favor of year-round boot wear, but know it can be challenging to style this family of footwear for warm weather.

If you’re pairing ankle boots with slim or skinny pants, try rolling a small cuff that hits just above the boot top, exposing a sliver of ankle. This provides a peek at the true silhouette of your leg, and also makes your overall look feel more seasonally appropriate. If you’re doing a dress or skirt and worry about visually shortening your legs, opt for a bootie that’s close to the color of your skin tone. Also accept that your eye may still be adjusting; ankle boots are still relatively new, and many of us aren’t used to seeing them worn with bare legs.

In terms of taller boots for spring and summer, I’d advise opting for light colors regardless of your skin tone. Knee-high black boots against bare skin won’t look terribly seasonal, but knee-high tan or cognac boots will be less jarring. Styling tall boots with cowgirl-influenced looks helps ease them into summer wear, too. Try a snap-front shirt and denim skirt, or floaty white dress and denim jacket.

Q: Tricks for working with extremely pale skin. I’m very fair — to the point where when I go without makeup, total strangers ask if I’m not feeling well. I’ve adopted the strategy of playing up my paleness rather than hiding it, but would always be happy for more tips.

A: I’m right there with you, my pale friend. I might not have the Scandinavian ancestry to back it up, but I rock Casper-white skin every day of my life.

First and foremost, my advice would be try not to worry about it. Anyone who has the time and energy to police the shade of your skin should really get a hobby. Your skin is your business, no matter how tan, not tan, pale, dark, spotty or covered in “Twilight”-reminiscent glittery bits it may be. Period.

Aside from that, try mixing more prints and patterns into your looks, especially up top. Big swaths of color can wash you out or alter how your skin tone is perceived, but patterns are more forgiving. Naturally, some patterns will work better than others with your hair, facial features and figure, so choose carefully. But be aware that doing patterns against pale skin may appear less harsh than solids.

When you do do solids, embrace contrast. Pale pinks, ivories and blushes may make you look uniformly ghostly, so opt instead for richer, more saturated shades that play off your natural undertones and offer sophisticated contrast to your light-colored skin.

You can also look to proudly pale celebrities for inspiration. Emma Stone, Cate Blanchett, Tilda Swinton, Nicole Kidman and Dita Von Teese all have fair skin. Any outfit photos you can track down will show you how they select colors, accessorize and style their hair to look stylish and chic year-round.

Q: Can you discuss the particulars of petites? I’ve never understood whether it just applies to the length of the clothes or whether it affects the overall garment in some way. I am short, but not necessarily “petite” in my frame, so sometimes petites work, but sometimes they don’t. I’d certainly appreciate it.

A: Great question, and one that isn’t often addressed directly. Most of us associate the word “petite” with height, and that’s certainly a factor. But clothing that is designed for petite frames isn’t just shorter, it’s designed for a set of proportions that diverges from standard sizing in several ways.

Most of us know that petite dresses and skirts have slightly higher hemlines, and that petite pants have shorter inseams. But you’ll find that most petite shirts are designed with shorter sleeves and petite pants tend to have slightly shorter rises. To accommodate a frame that is more compact, petite dress waistlines are often a little higher than those of regular sized dresses. And in really good petite lines, designers will have adjusted knee placement to suit shorter legs.

So if you’re a regular-height person with a short waist, you can try buying petite tops. They’ll certainly be shorter in the body, but those shortened sleeves may look a little odd on you. And if you’re over 5 feet 4 and your long-waistedness affects your pant hems, you might want to go with a short inseam instead of switching over to petite sizes.

Sally McGraw is a Minneapolis-based personal stylist and creator of the Already Pretty (alreadypretty.com) blog. Her fashion advice appears on this page once a month. Send questions to: [email protected]

Getty Images

Fashion may not always make sense, but it sure is fun to experiment and play dress-up—especially when it comes to trends that are completely unexpected. One of the latest not exactly utilitarian trends to emerge via our favorite style stars, like Olivia Munn, Khloé Kardashian, and Kylie Jenner, may seem crazy to even consider, let alone actually wear during the dog days of summer—but we’ve got to say, it looks so cool. We’re talking about suede boots, knee-high and thigh-high styles to be specific. Sure, you’ll need to put them on in a fully air-conditioned room, and yes, you may need the help of a friendly neighbor to pull them off at the end of the day, but we’re thinking the look is awesome enough to warrant the extra effort.

How to wear suede thigh high boots in the summer? Rock them with super-short jean shorts or boxy minidresses, for the ultimate It Girl look. Take a look at how these celebs are wearing summer boots for inspiration, and shop some styles below.

Khloé Kardashian

Splash News

Kylie Jenner

Getty Images

Olivia Munn

Getty Images

Styles we love:

Steve Madden, $100

Pixie Market, $89

Stuart Weitzman, $798

Kristen Cavallari, $349

ASOS, $123

Ruche, $60

Now, watch 14 times your fave celebs—oops!—forgot their pants.

Cost Of Healthy Living

There are some things you just shouldn’t wear in the summer. Fur coats, wool sweaters—anything that’s guaranteed to make you sweat and stand out like a visitor from Antarctica. But one of the most contested items of possible-summer fashion is the knee high boot. Can you wear knee high boots in the summer? Or perhaps more importantly, should you wear them in the summer? If you’re staring at your favorite pair of knee high boots, standing alone in the corner of the closet like an unloved present from your favorite Aunt, don’t fret: it is possible to wear knee high boots in the summer and not look ridiculous. How? Let’s take a closer look at how you can wear them in the summer, and why it won’t make you a social pariah among your fashion oriented friends.

Styles of Knee High Boots

The image that most people might conjure up when considering knee high boots are classic stompers: those thick, almost military style black boots that look as intense and impressive as any army commander. But there are actually many different styles of knee high boots, which range from those classic army stompers to stiletto heeled evening boots to dainty cut out lace up knee high boots with an almost delicate look to them. In other words: not all knee high boots were created equally. You might look strange if you showed up to a summer event in thick black military knee high boots—but not if you showed up wearing the latest off-white cut out lace up knee high boots, just recently seen on celebrities such as Selena Gomez, Lady Gaga, and so much more.

Look for Weather-Friendly Materials

Before you take your boots out of the closet, consider what kind of material they are made out of and the current weather conditions. Most places get at least somewhat hot in the summer, which is what makes it necessary to tailor your wardrobe to the weather. If it is hot, take a closer look at those boots. Is the material thick? Is it heavy? Are the boots insulated? If the answer to any of these questions is yes, and the weather is warm, you will really want to leave them at home. Click to find 10 most beautiful cut out boots for summer.

Instead, look for boots with summer-friendly designs. And yes, cut out lace up knee high boots are great for summer; the cut out design will help prevent your legs from getting unnecessarily sweaty, for one, and these types of boots are typically made out of thinner material in order to allow for the cut out designs.

Great fashion couldn’t happen without great risk. If you think a pair of knee high boots would perfectly compliment your outfit, even if the style doesn’t exactly scream “summer,” then take a chance and wear them out! Who knows? Maybe your outfit will be the one that sparks a new trend for different styles of knee high boots in summer ensembles!