How To Wear Over-The-Knee Boots

Written by Sophie Diego

Sophie Diego

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Ankle boots, with their ‘pumpkin spice’ aesthetic, may seem rather comical compared to their thigh-high counterpart.

Of course, these cropped fall boots will always have a place in our hearts, but it’s natural to crave something different. Thanks to trendsetters such as Ariana Grande, Rihanna, and Kim Kardashian, over-the-knee boots are now the talk of the town. 

Recognized as a sultry way to start an outfit, these shoes exude a ‘boss bitch’ attitude to those who wear them. Also, they help provide a hint of edginess to any look—ranging from baby doll dresses, and mini skirts to the classic pair of jeans.

Obviously, there are different designs to choose from, which leads us to the ultimate dilemma: how to wear over-the-knee boots. 

Looking to jump on the fashion bandwagon? If so, I’ll show you how to wear over-the-knee boots using 10 outfit ideas. After reading this article, hopefully, you’ll know all this and more:

• How to wear over-the-knee boots over 40 
• How to wear over-the-knee boots to work 
• How to wear over-the-knee boots with jeans 
• Over-the-knee boots for women outfit ideas 

When To Wear Over-The-Knee Boots

Before I address how to wear over-the-knee boots, I thought it best to address the whens first. Generally speaking, this specific shoe is worn casually. 

Considered a closet staple for streetwear, minimalism, maximalism, and Instagram baddies, this particular cut helps to sharpen any ‘mundane’ look.

If your outfit is missing a little somethin’ somethin,’ chances are that you’re in dire need of some fancy boots. 

Due to their full-coverage silhouette, over-the-knee boots are typically worn during the cooler seasons. They’re designed to conform to the shape of your legs, so they don’t provide much breathability in warmer climates. 

History Of Over-The-Knee Boots 

Sorry, Ariana Grande. You weren’t the first to popularize the over-the-knee silhouette. In fact, it’s been around since the 15th century. Typically showcased in paintings, the elite was often depicted wearing thigh-high boots. 

They were primarily meant for men and horseback riding since their full coverage design helped to protect the legs from chafing and scratching.

They were also adopted as part of early military uniforms as soldiers left behind their heavy metal armor for lighter alternatives instead. 

Over-the-knee boots became widely popular in the 19th century. Their association with menswear and the military uniform began slowly fading as they became a sex symbol for London prostitutes.

Their sexualization soon transformed from comical to couture in the 1960s, when Yves Saint Laurent included them in his early clothing collections. 

Today, over-the-knee boots are worn as part of casualwear. Of course, the word ‘casual’ can be interpreted in many different ways.

Nevertheless, these shoes are considered an important closet staple for many core aesthetics. 

How To Wear Over-The-Knee Boots

The simplest way to answer the ‘how to wear over the knees boots’ question is to do it with confidence. Theoretically, this type of shoe can go with any outfit, but it does require a dose of braggadocio in order to pull it off. 

You can rest assured that the ensembles I’ve featured will help you show off your swagger. Ranging from mini dresses to full-coverage pants, these outfits are stylish and bold. Let’s check them out. 

10 Outfit Ideas With Over-The-Knee Boots

Shirt dresses and oversized blazers are the go–to fit for many Instagram influencers. Is it basic? Perhaps, but I can’t deny how cute this ensemble is.

Accentuated with a belt, a black hat, and a pair of over-the-knee boots, it’s the kind of look that comes with a #Paris location tag. 

If you’re gearing up for fall, I’d recommend layering with sheer tights for a bit of coverage. For accessories, you can never go wrong with an adorable crossbody bag. 

You can never go wrong with a classic mini skirt. Given that over-the-knee boots are quite bold in aesthetic, it’s important to balance out the outfit with another statement piece.

For instance, a houndstooth trench coat can help mellow out the braggadocio tone of the shoes. 

You don’t need to opt for a busy blouse, since a simple black shirt can complement the final fit nicely. Best paired with sunnies and a cute bag, this ‘how to wear over-the-knee boots’ contender is definitely ready for Instagram photo ops. 

The ‘it girl’ aesthetic requires full fashion commitment. Case in point, this bold outfit consists of a zip-up pullover, cargo shorts, and a pair of over-the-knee boots wide calf shoes. 

Of course, brown isn’t the most bright color to choose when it comes to clothing.

But the silhouette of the ensemble enhances the entire look, as it nearly showcases a fit and flare shape thanks to the cropped sweater and fitted bottoms. Oh, and the boots? They work wonders by elongating the legs. 

Most answer the ‘how to wear over-the-knee boots’ question with a simple mini dress or skirt. Of course, there’s nothing wrong with opting for either, but you shouldn’t forget about midi dresses. 

Considered another way to style thigh-high cuts, this outfit can help provide the illusion of length. I highly recommend wearing sweater dresses to exude a warm autumn vibe.

Of course, this ensemble wouldn’t be complete without a black leather jacket and crossbody bag. 

Cowboy boots are all the rage this season. Given their popularity, it would be a disservice for me to not include an example on my list. Paired with mid-wash jeans, this rustic look features a black tee and an oversized green bomber jacket. 

It’s super casual in aesthetic, so it could be a great OOTD for running errands. Since this outfit is quite bold, I don’t recommend adding any accessories. They may overshadow the beauty of this simple ensemble. 

Ultimately, it doesn’t matter if you’re 20, 40, or 70. You can still rock a pair of thigh-high boots.

Take, for instance, the legendary Anna Wintour. She decided to pair her leather kicks with a matching trench coat and a stunning geometric dress. 

Accentuated with her iconic black sunglasses and bob haircut, this is definitely the real-life version of Miranda Priestly in The Devil Wears Prada.

For accessories, this ‘how to wear over-the-knee boots’ guide highly recommends adding a cute handbag. 

Let’s be honest. Office attire is quite boring in aesthetic. If you’re looking to kick things up a notch, I recommend this over-the-knee boots black outfit. 

It features a pair of suede thigh-high kicks, jeans, a matching sweater, and a cute brown handbag. Of course, this ensemble is only geared for ‘informal’ workplaces, such as fashion magazines. If anything, it can make for a cute casual Friday get-up. 

Looking for over-the-knee boots flat heel outfit ideas? No worries, I’ve got you covered. This cute OOTD showcases a pair of platform stompers with a slim-fit mini skirt. 

The turtleneck crop top helps to accentuate the waistline, while the trench coat provides the illusion of height.

In my opinion, this ensemble makes for a great autumn look for those not fond of the ‘pumpkin spice girl’ aesthetic. Don’t forget to top the whole look off with a clutch bag. 

Thigh-high boots look good on men—no questions asked. If you’re looking to up your clothing game, I highly recommend this loud and proud outfit. 

Composed of red latex stompers, a black The North Face jacket, and a matching puffer coat, it’s definitely a bolder take on casual athleisure.

This is the kind of ensemble that’s meant to make a statement, which is perfect for those who don’t conform to binary fashion. 

The couch potato aesthetic and thigh-high boots are considered polar opposites on the fashion spectrum, right? Contrary to popular belief, this unique combo is all the rage this season. 

Popularized by the likes of Ariana Grande and Hailey Bieber, it’s the perfect go-to for trendsetters who can’t be bothered.

It’s worth noting that this look can only be accomplished with oversized clothing—such as an extra-large hoodie and a puffer jacket. 

What Type Of Over-The-Knee Boots Can You Get?

The best way to cure a styling slump is to consider the options you have. Fortunately, there’s no shortage of cute over-the-knee boots on the market, so trendsetters can choose from various silhouettes. 

From cowboy stompers to chunky platforms, there are so many options to choose from. So, you might be feeling a bit overwhelmed. Luckily, I’m here to make things simple.

This ‘how to wear over-the-knee boots’ guide will feature a few common trends worth considering. 

• Cowboy boots: In the mood for some Western flair? If so, you can never go wrong with a pair of cowboy boots. I highly recommend opting for a decorated pair, such as the classic paisley print. 
• Skin-tight leather: Considered the OG of all thigh-high boots, these shoes can help add a sexy vibe to any outfit. 
• Latex stilettos: If you really want to up the sexy factor, these can be your go-to shoes. It’s worth noting that you may need corn starch to help make the removal process easier. 
• The animal skin boots: Often featuring snakeskin or crocodile print, these shoes can help give your outfit an exotic look. 
• Classic suede: New to thigh-high boots? If so, I believe opting for this specific design if you want to keep things casual. 
• Platform stompers: Perfect for Insta-baddies and grunge enthusiasts, these shoes are considered an edgier version of your usual Doc Martens. 

How To Choose The Best Over-The-Knee Boots 

Fast fashion is quick, convenient, and widely affordable. Finding a $40 pair of over-the-knee boots is nothing to brag about, given the wide amount of cheap options on the internet. 

While you’re free to go after bargain deals, you may find yourself discouraged by the shoes’ short lifespan.

Counterfeits, knock-offs, and heavily mass-produced shoes are known to be poorly constructed, which is why it’s important to don your responsible shopper hat. 

If you value sustainability, it’s best to consider four factors when shopping: material quality, comfort, design, and price. In terms of over-the-knee boots, reputable brands usually source genuine leather, animal skins, and suede for their fabrics. 

Depending on their style, these shoes are typically structured in silhouette and flexible when worn. Material quality also relates to key features such as zippers, elasticated inserts, and the strength of the heel.

Comfort usually depends on the heel of the shoe. If you can walk in five-inch stilettos with no problem, then there’s no need to worry about balance, foot pain, and overall walkability. 

But for those who can’t manage a single step, it’s probably best to opt for flat soles as a safer alternative. Trendsetters should also consider their lifestyle, as I don’t recommend wearing dagger pumps for everyday commuters. 

In terms of design, shoppers should consider their current aesthetic before settling on a pair. It’s worth noting that I’m not specifically referring to the color and print of the shoes.

The silhouette also plays a pivotal role, as trendsetters can choose from loose to tight cuts. 

In addition, some over-the-knee boots come with additional embellishments such as tassels, sequins, and stitching details, which may not blend easily with the average capsule wardrobe. 

Material quality, comfort, and design depend heavily on the price. Of course, this is not to say that designer brands are the only way forward. You can easily find a pair of boots for a reasonable price.

I’d suggest sticking to a $200 to $300 price range to ensure that your shoes are well-made yet still affordable. 

How To Style Over-The-Knee Boots Outfits

Consider yourself briefed on how to wear over-the-knee boots. Given their bold silhouette, accessories are no longer an option—they’re now a requirement.

For those in need of additional outfit tips, I’ll explain how to style these specific stompers next. 

1. Sheer tights: Although they’re meant to cover the entire leg, there’s no harm in wearing a pair of pantyhose for extra coverage. 
2. Mini dresses and skirts: If you’re looking for a simple way to style these shoes, I recommend donning the over-the-knee boots with dress look. 
3. Hair buns: This may seem like a strange styling tip, but trust me. This specific hairstyle paired with over-the-knee boots exudes a level of sophistication and class. 
4. Leather jackets and trench coats: Considered a simple way to style thigh-high boots, these particular garments help to even out the boldness of black leather. 
5. Simple jewelry: As previously stated, over-the-knee boots are quite bold in aesthetic. With that in mind, it’s best to stick to simple accessories to keep things casual. 
6. Dainty handbags: Instead of opting for backpacks and large totes, small purses are a great way to elevate the final fit. 

Fashion Tips To Avoid With Over-The-Knee Boots 

Don’t get me wrong. I’m all for a bit of fashion experimentation. That said, there are a few fashion no–no’s associated with this particular shoe.

For those who need a style ‘de-briefing,’ this ‘how to wear over-the-knee boots’ guide will share some fashion tips to avoid. Hopefully, they’ll help save you from post-Instagram regret. 

• The Y Project Uggs: This controversial collab combines the classic Ugg with thigh-high boots. The result? A Frankenstein design that’s unflattering—roll after roll. 
• Latex boots for the long term: If you’re gearing up for a photo shoot, these shoes can help elevate your look from 8 to 10. However, I don’t recommend donning these kicks in real life unless you’ve prepped your legs with corn starch. 
• Peep-toe boots: Just imagine wearing these shoes during a snowstorm…just imagine. 
• The ‘butt-cut’ boots: If your shoes extend past the crotch era, there’s a good chance that they should be reserved for Coachella only. 
• Ball gowns: Unless you intend on making a statement, I’d suggest swapping your thigh-high boots for a regular pair of stilettos instead. 
• Loose pants: If you’re keen on wearing skin-tight thigh-highs, it’s probably best to wear skinny jeans or leggings in place of denim bell bottoms. 

How To Take Care Of Over-The-Knee Boots 

Congrats, you finally know how to wear over-the-knee boots. Given your excitement, it’s natural to assume that you’d like to take good care of your coveted pair—especially if your beloved boots have gone through hell and back.

For those in need of some cleaning suggestions, I’ll provide a few tips and tricks to help maintain the boots’ quality. 

• Use a microfiber cloth to eliminate surface-level dirt. You can also use a gentle brush for stubborn debris. 
• Spot-clean stains with a damp rag. I’d suggest using a bit of soap to help make the removal process easier. 
• Condition with leather solution. It’s worth noting that this does not apply to other materials. 
• Store in a dry and dark place. Excess heat and sun exposure may ruin the quality of your boots over time. 
• Stuff with newspaper to help maintain their shape. You can also use a boot shaper as a more efficient method. 

Best Places To Buy Over-The-Knee Boots 

Before this ‘how to wear over-the-knee boots’ guide ends, I’d like to leave my readers with a few store recommendations:

• Nordstrom 
• Naked Wolfe 
• Jeffrey Campbell
• Stuart Weitzman 
• Franco Sarto 

Final Thoughts

Despite my go-getter attitude towards fashion, I completely understand if you find over-the-knee boots too daunting.

Their slim-fit silhouette and sharp heel make for a bold statement piece, which may seem too ostentatious for some novice dressers. 

That being said, style requires confidence, determination, and creativity. This isn’t the time to narrow down your options, as fashion is meant to get you out of your comfort zone. 

I’m fairly certain that my ‘how to wear over-the-knee boots’ guide has instilled you with enough inspiration. From mini dresses to blazer suits, there are hundreds of different fits to consider for your next Instagram post. 

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