Got Thigh High Boots? Here’s How To Style Them This Fall

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Preparing for fall? We hope you have your thigh high boots ready! If you’re finding them hard to style, this guide on what to wear with thigh high boots will be useful for you.

Fashion girls know this: thigh high boots are a fall must-have for a chic look. Whether you’re in search of something to wear to the office or on the prowl for a new date, thigh high boots can get you just about anywhere. And while we all know that these babies will keep your legs warm on cold days and give them some shape, they also offer an endless number of outfit possibilities, especially in the winter months!

This post is dedicated to showing you how to dress up your favorite pair of thigh highs with different styles and trends that will have you reaching for your wallets.

A pair of thigh-high boots should be a staple in any woman’s wardrobe. They add a touch of glam to any outfit, and they’re also great for making an outfit feel edgy and sassy. They can add warmth not only to your feet but to your thighs as well, so if you live somewhere where the seasons are harsh, then it’s time for you to get your own thigh high boots to keep you warm and snug.

The awesome thing about thigh high boots (especially the heeled ones) is that they automatically elongate your legs, making you seem taller than you are. Below, we made you a style guide on some amazing thigh-high boot outfit ideas.


What To Wear With Thigh High Boots (& Look Chic)

1. Sweater Dresses


What to wear with thigh high boots: cute sweater dresses

Shop this sweater dress at Magnolia Boutique


Since it’s fall season and the days and nights are slowly getting colder, sweater dresses are the number one most popular option to wear with thigh high boots. We especially love a good turtleneck sweater dress for cozy looks.

Oversized sweater dresses will keep you snug and comfortable, while the boots will offer an extra layer on warmth and edge to an otherwise simple outfit. But if you’d rather go for a short dress with a different style, you can pair it with long trench coats, and opaque tights underneath the dress and the boots.


2. Skirts Or Dresses With Volume


What to wear with thigh high boots: floral skirts with ruffles

Shop this look at Mint Julep Boutique: Skirt | Top | Boots


Skirts and dresses with lots of ruffles or volume work great with thigh high or knee high boots. This look is not as warm as our previously mentioned sweater dress looks, but they are just as cute.

If you are looking to style thigh high boots in a classy and sophisticated way, adding lots of layers and ruffles will balance out your whole outfit.

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3. Pencil Skirts


Burgundy corduroy skirt with black top and black leather boots

Get this skirt on Shein


You can pair thigh high boots with a mini pencil skirt, a pair of black stockings underneath, a snug long-sleeve turtleneck top and a badass leather jacket, and you got yourself a whole baddie fall outfit. Who says you need to be all covered up during the cold season? With the right clothes and the right layers, you can still be your fashionable self while staying safe and warm.

Another outfit idea involving skirts would be a nice leather skirt and a tucked-in oversized sweater. To elevate your look, pair this with snake-print thigh-high boots to break up an otherwise monochromatic look.

When you are styling thigh high boots with skin tight skirts, make sure that there’s some balance to your outfit: add a leather jacket, blazer or a chunky knit, so that your whole look isn’t skin tight – this looks cuter and classier!


4. Leggings Or Jeans



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A post shared by Maria Vizuete • Mia Mia Mine (@miamiamine)


You can most certainly pair thigh high boots with leggings or jeans for a casual look! Since leggings are snug, thin, and they stick to the skin of your leg, this makes them easier to wear under thigh high boots than jeans.

If you want to wear jeans, you have to make sure to get a pair of skinny jeans so it wouldn’t be too bulky. Top this with chunky sweaters and black thigh-high boots, and you’ve got an outfit!


5. Midi Skirts


Cute midi skirt outfit with boots for fall

Image & outfit via Chic Wish (Shop the skirt there!)


Midi skirts are another good idea, and you won’t have to wear stockings underneath since midi skirts fall just past the knee anyway. Chic tip: Get a midi skirt with a high slit on the side, so you can still show off your gorgeous thigh high boots (and show off a sliver of skin). To keep warm, layer your entire outfit with a long coat.


You might find a few of the outfits below to feature knee-high boots instead of thigh high ones. Don’t stress – these outfits work with any variations of boots! 


10 More Outfits To Wear With Thigh High Boots




What to wear with thigh high boots: Turtleneck oatmeal sweater dress with snake print boots


Get this dress on Princess Polly




What to wear with thigh high boots: sweater dresses


Get this dress at Magnolia Boutique




What to wear with thigh high boots: Baby blue sweater dresses


Get this sweater dress on Princess Polly




What to wear with thigh high boots: floral ruffle skirts


Get this look at Mint Julep: Skirt | Sweater | Boots | Hat




Black drawstring sweater dress


Get this dress on Princess Polly




Cute color block sweater dress with over the knee boots


Get this color block sweater dress at Shein




Cream long-sleeved midi dress with white boots


Get this dress on Princess Polly




Red corduroy pencil skirt with black boots and black top


Get this skirt on Shein




White sweater dress


Get this dress on Princess Polly




What To Wear With Thigh High Boots: Simple long-sleeve sweater dress with beige thigh-high boots


Get this dress on Lulus


Commonly Asked Questions


Can thigh high boots be worn in any season? 

Absolutely! You can wear them in both winter and fall to provide warmth for your feet and legs, and you can also wear them in the summer and spring as well, to add a touch of edginess to your short skirts or mini dresses.

Basically, thigh-high boots can be used for everyday wear. It all depends on your styling preference! (Pro tip: Invest in a good pair of snake print boots with block heels! This bold pair goes well with different occasions, and can even be worn on dates).

Are thigh high boots still in style this year? 

Thigh high boots are always in style, no matter what year, which is why it’s smart to add a nice pair (or two!) to your closet. Thigh high boots are surprisingly versatile, and you know about fashion styles – they evolve every year. Thigh high boots will always adapt to emerging fashion trends. 

What socks do you wear with thigh-high boots?

While you can wear any socks that you want with thigh high boots, over the knee socks or knee high socks are best for keeping you warm. If you’re boots are very snug, opt for shorter socks instead.


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