Thigh-high boots are a fun pair of shoes and have been quite on trend for years. They are a great pair for a night out, but can be worn during the day too, particularly in the colder months, since they go all the way up to your thighs. They are a super stylish type of footwear, can can work for different occasions, depending on how you choose to wear them.
If you wear thigh-high boots in the right outfit, they can take you from the office, depending on how your dress code at work is and what you’re allowed to wear there, to a date, or to a girls’ night out, you name it. It is critical to pair thigh-high boots with the right pants and coats, to create the feminine and classy outfits and avoid looking provocative.
If you’ve been looking for some fashion inspiration on how to wear them, here’s what to wear with thigh high boots:
Wearing jeans with thigh-high boots can create a casual or edgy look. Without saying, jeans are the easiest pair of pants to wear, especially if you want a laid back look, and they can also be dressed up. They’re versatile to be worn to different places, and regardless of your body type and size, you can be sure that there’s a pair of jeans meant just for you.
If you choose to go with a leather jacket, jeans with thigh-high boots has the fashion-forward edgy vibe. If you simply go with a t-shirt on top, this combination is perfect for everyday wear. This pairing can also be dressed up, if you wear your jeans with a button-down or a blazer.
While there are many different types of jeans to choose from, your best alternative for an outfit with thigh-high boots is a pair of skinny jeans. They follow the shape of your body and since they’re skinny, they will fit right into your boots seamlessly.
Megan (above) wore her blue jeans with thigh-high boots.
You can tuck in sweater like this and go for a simple nude bag. When styling thigh-high boots with jeans, it’s the contrast between the jeans and thigh-high boots that makes the look more interesting.
With an over coat
A warm coat (whether it’s an overcoat or classic trench) easily gives you that fashion blogger’s off duty look. It’s a great wardrobe piece to own as it works for those cold nights or during fall but still looks chic as it shields you from the cold. It’s worth pairing them with some thigh-high boots for some extra warmth.
Women’s coats can be made so many types of fabrics and thickness, and also come in different lengths and colors. You can choose a pair of thigh high boots that match your coat color for a monochromatic look. Alternatively, you can go for a contrasting color of boots just as long as the colors go well together.
Askale (above) wore her trench coat with some suede thigh-high boots. You could have the trench coat open so that whatever you’re wearing underneath is also seen but you could also let your trench coat make the statement by closing the buttons at the front.
With an A-line skirt
A-line skirts are great pieces to wear with your thigh-high boots. A-line skirts are feminine and flirtatious. They’re great as they hide the bits of your body that might be a little bulgy, i.e., you will feel more confident when wearing them especially if you get the length right.
The thigh-high boots just have a way of transforming the look from feminine and dressy to a bit laid back, which is great. Choose the skirt length you are most comfortable with. Weather it is mini, midi or even maxi length, A line skirt always works wonders on any body type.
If your goal is to elongate your legs, the best way to go about it is to ensure that your A-line skirt is shorter so that it does not cover the boots, for a more flattering look.
Kendall (above) wore a fun feminine A-line skirt with a white sweater and matching brown boots.
If you are going for a printed A-line skirt, it’s always better to go for a plain pair of boots. Matching colors are an easy way to go about this style if you’re not exactly used to wearing thigh-high boots as it’s less of a risk.
With a fit and flare dress
Wearing your thigh-high boots with a fit and flare dress is an amazing way to look both cool and feminine. Just like an A-line skirt, a fit and flare dress (sometimes known as skater dress) is super forgiving since it hides a lot of flaws. It is also very flattering since it brings attention to the tiniest part of a woman’s body, the waist. These dresses can be worn to just about any place you find yourself in whether church, an office, the club, a party and so many others.
Once again, a shorter length does the trick better if you want both your boots and the dress to stand out on their own. You could go for a sleeveless skater dress and layer a shirt or a turtleneck underneath it for a preppy fall look. You can also look grungy by layering a plaid shirt over the dress. There are many options so it all depends on your preference.
Muireann (above) styled her printed skater dress with some black thigh-high boots. Black thigh-high boots allow for your dress to stand out especially if it’s printed or comes in a unique design around the sleeves or neckline.
With a shift dress
A shift dress is one of the most comfortable dresses one can find and it gives you a great silhouette as well. After all, it was designed to be a lose fitting piece of clothing, therefore, hiding any part of your body that you might feel still needs some work and only brings out the best. Shift dresses go with thigh-high boots quite well thanks to their flowy nature.
Remember, the boots follow the shape of your legs too, so this is an outfit that is automatically balanced. You can wear the shift dress in different colors, prints or patterns but go for a muted thigh high boot or vice versa. Feel free to accessorize with a hat or some statement earrings to make the outfit more interesting.
Lyra (above) wore her leopard print shift dress with her black thigh-high boots and a black bag. Shirt dresses are available in different prints and they can all be paired with plain black thigh-high boots regardless of how feminine they might be.
With a leather skirt
Leather skirts come in different types and it’s up to you to choose one that suits your personality most. You can get a leather skirt suited for the workplace or a more formal event, these aren’t too shiny, or get the ones that stand out more. Whichever you choose, you can pair your leather skirt with your thigh-high boots too.
A slightly longer leather skirt worn with a button down can work for an office environment (assuming the dress code is not as strict). You can pair your skirt and boots with more casual pieces like denim jackets for a day out. For a night out with the girls, a shimmery looking, shorter leather skirt paired with your thigh high boots will not only have you looking great but will also help you stay warm.
Hana (above) wore her leather skirt with a black turtleneck and a pair of suede thigh high boots. Remember, just because your skirt is leather does not mean you have to wear leather boots too. Any other material can work just as long as the colors of your outfit go well together.
With a shirtdress
A shirtdress is often seen as a smart dress that women like to wear, especially if they want a bit of a serious look. Shirtdresses look sassy when worn with a great pair of heels, they look laid back styled with sneakers and edgy when worn with booties. You can wear a shirtdress with your pair of thigh-high boots for an effortlessly chic look.
This is especially great because it can be a bit challenging to wear dresses in colder times. You can go ahead and layer a pullover over your shirtdress for this look to feel even warmer and to achieve a more preppy look, in case your shirt dress is plain and in a simple color such as white. With a shirt dress, you can also go for a leather jacket that matches your boots for an edgier look.
Imani (above) kept her outfit classic and simple by wearing her black thigh-high boots with a loose-fitted white shirtdress and a black bag. You can also pair your thigh-high boots with a more fitted shirtdress.
With a sweater dress
If it’s cold outside, then one of your best bets to keep warm is a pair of thigh-high boots paired with a sweater dress. Sweater dresses are relaxed and cozy enough to make you want to get all snuggled up already. They’re also very stylish considering they’re available in different styles such as turtle necked ones, more fitted ones or even fitting ones that almost resemble bodycon dresses in style.
For most people, the biggest concern during colder times is that you might have to hide your fancy dress under a huge coat, but that’s not the case here. You can go for a fancier sweater dress with volume then layer something underneath it instead, that way the dress is not hidden. Choosing a high heeled thigh high boot makes you look even dressier.
When you go for printed boots, it’s better to wear a neutral color sweater dress or pick a sweater dress whose color is also on the boots.
With a leather dress
A leather dress is one of those dresses that make you feel unique, provided you pick real leather and not the faux leather type. Genuine leather fabric also lasts longer and will be able to give you value for your money. The best part about leather dresses is that they can also be paired with your thigh-high boots.
Remember, leather is classic and will never go out of style, so, buying a dress in genuine leather is a great investment. While many think leather is only available in black, white and brown, this isn’t true as you can buy yourself a leather dress in other fun colors such as yellow, green, and red just to mention a few. This makes it easier for you to come up with a fun outfit when you pair the dress with thigh-high boots and will have you standing out in that cool, fall weather.
Style Professor (above) wore her leather thigh-high boots with a leather dress and leather gloves. This is a daring pairing considering the dress covers the boots partly. Leather boots work well with a leather dress however you could go for boots in other materials such as velvet for such a pairing. The boots don’t have to be black either. You can play around with colors.
With leather leggings
You can also wear your leather leggings with your thigh-high boots. Leather leggings are daring and many often shy away from them. However, when they’re styled right they make an outfit more chic.
Going for black leather leggings allows you to wear different thigh high boots such as printed ones. A leopard print or perhaps a snake print pair of thigh high boots will make both the leather leggings and the boots stand out. You can also opt for different materials such as denim thigh high boots or go for leather ones. Leather boots and leather leggings worn together will make you look taller since the pairing gives the illusion of longer legs.
Patricia (above) wore her leather leggings with some black thigh-high boots, a button-down, and a blazer. Darker colors of leggings, boots, and a blazer have a way of making you look effortlessly chic as the colors are classic.
With regular leggings
A lot of women stock up on regular, simple leggings because they are comfortable. With them, you can also conform to any style you want because they are highly versatile.
If leather leggings are too much of a stretch for you, there’s good news. Your regular leggings can also be paired with thigh-high boots and the best thing about this is that they allow your amazing boots to stand out. In fact, the simplicity of your regular leggings allows you to also throw on more statement pieces on top that will go great with your thigh-high boots.
With this thigh-high boots with regular leggings pairing, you can always go for something fancier on top and not just a sweater. This is because the leggings are minimalist.
With a tulle skirt
Believe it or not, the girly pieces that are tulle skirts can actually be worn with thigh-high boots. When there’s an occasion that needs you all dressed up, one of the easiest ways to go about it is to grab a tulle skirt. While it’s easy to end up looking like a little girl at a party in a tulle skirt, it’s also possible to look all classy or edgy in one.
It’s a bit of an unexpected combination but what matters is that the boots work well enough to add a touch of edginess to the look. You can go ahead and add a denim jacket or a leather one on top to give your tulle skirt an even more casual and grown up feel.
A sheer tulle skirt is an excellent choice for this pairing as it allows the boots to be seen especially if the tulle skirt is long.
With a jersey dress
A jersey dress is a great sporty dress that resembles an actual jersey shirt. It’s a great piece to own as it gives that androgynous look that’s flattering to the female body regardless of the shape.
While most people will think of wearing a jersey dress with some sneakers, wearing them with thigh-high boots gives the jersey dress some extra power as it toughens up the already sporty look more. You can get one in a more A-line shape or just go for a straight, boxy style jersey dress for this pairing. You can also choose one with sleeves or one that’s sleeveless.
It’s a simple pairing, however, you do not have to wear a black jersey dress every time. They exist in many different colors all of which work well with thigh-high boots.
With a bodycon mini dress
You can wear your bodycon dress with thigh high boots for a night out. A bodycon dress is figure-hugging all the way from the top to the bottom, and wearing one is the ultimate sign of self-confidence. This is because it makes a bold statement by showing the exact shape of your body, every curve of it. This outfit is a great combination if you’re going to be in a club all night with your girls or on a date.
This combination also fits in perfectly if you’ll be at a concert. However, if you don’t mind turning heads during the day, you can wear a bodycon dress with your thigh high boots too.
When the weather gets chilly, you could always add a pair of tights underneath your dress. If it’s a bit cold outside, you can also throw on a coat or jacket to make the look more daytime appropriate.
Gabbi (above) wore her blue bodycon dress with black thigh high boots. For this, always make sure the dress fits you properly and doesn’t ride up as that could make your outfit look trashy, which you don’t want.
With short shorts
Short shorts are a great way to show off your legs especially during summertime. They are available in different styles with denim ones being the most common. If you would still like to wear your short shorts into the fall, they could actually make for a nice transitional piece when worn with thigh high boots.
The shorts give the boots a good balance, compared to longer shorts, because longer ones could sometimes hide part of the boots and make you look shorter. If you would like some extra warmth, you could also wear some dark tights under the shorts.
Solie (above) wore her snake print pair of thigh-high boots with short shorts and a crop top. You don’t always have to go for a plain pair of boots as such minimalist short shorts give the best opportunity for you to try out different prints.
With a sari
A sari is a traditional style dress that is popular among women of Indian, Pakistani or Sri-Lankan decent. It’s very feminine and can be draped on the body in a number of styles.
While it’s commonly worn with more feminine pieces, you can wear a sari with thigh-high boots to give it that unexpected look. Saris are often colorful and full of embellishments. As such you need to give the outfit a good balance by going for simpler thigh high boots. The most interesting thing is that you can actually choose from several different colors that saris come in so you are assured of an interesting outfit.
Sneha (above) wore her sari in a more modern way with her thigh-high boots. Layering a turtleneck or a t-shirt under the sari makes the look more casual considering how fancy saris usually are.
With a midi skirt
Styling a midi skirt can be quite challenging because of their length since they fall between the knees and ankles, which is why many shy away from them. However, when done right, a midi skirt will have you looking ready for any kind of setting. While most people will prefer shorter skirts for a thigh-high boots pairing, you can actually wear a midi skirt with your thigh high boots.
For this, going with a skirt that has a high side slit is the best option as it allows you to show the full design of the boot and at the same time, the slit gives your otherwise simple midi skirt some character.
Giselle (above) wore a button-down midi skirt with some snake print thigh-high boots and a plain top. It’s worth trying out a crop top since, with a midi skirt and thigh-high boots, your body is mostly covered. A crop top and a slit make the outfit a little less bulky-looking.
With a blazer dress
Just like a blazer, a blazer dress has an amazing clean type of silhouette that always looks chic. They come in different lengths that are flattering for different pairings.
A great way to style blazer dresses is with thigh- high boots. This pairing gives you that Parisian chic look especially if you wear a beret or any other hat along with the outfit. This pairing is also great for events and a night out. You just need to balance the colors of the boots and blazer dress so that you don’t end up looking overdressed or like there’s too much happening with your look.
Katarina (above) styled her blazer dress with some snake print thigh-high boots. Colors such as black and white for the blazer dress add more sophistication to such an outfit although you could go for brighter colored blazer dresses.
With a T-shirt dress
A T-shirt dress (sometimes also known as jumper dress) is not only cozy and comfortable, but is also a great piece to add to your fall and winter wardrobe if you’re tired of your regular dresses. They can actually be either very chic or edgy depending on what you choose to wear them with.
Pairing your jumper dress with thigh high boots is a great way to look hot and ready to turn heads when you step out. You can go for a loose-fitting one and add a waist belt if you feel like your waist could get lost in it. Alternatively, you could wear it baggy just like you would with a shift dress.
Thandolwethu (above) styled her jumper dress with some thigh-high boots and a baker boy hat, all in black. Matching the material of your hat and the thigh-high boots gives such a look more balance as it makes the outfit look cleaner.
With a matching sweater set
A co-ord set makes dressing up or down easier since it refers to two matching pieces of clothing that come together. You, therefore, don’t have to think too hard about how to match your different clothing pieces.
Wearing a skirt co-ord set with your thigh high boots is a great idea since you will not struggle to get the boots all the way up. The same can be done with a pants set just as long as the pants are skinny. You can go for contrasting colors for the co-ord set and boots but you can also pick matching colors or similar shades for a monochromatic look.
Kristina (above) styled her co-ord set with thigh-high boots and a simple black bag. A co-ord set when paired with such boots always looks well put together and you can choose from different sets. You could go for more casual ones or dressier ones.
With these twenty styles for inspiration, you should feel more confident to try out the thigh-high boots trend as it could easily end up becoming a favorite for you.