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10 Styling Ideas To Wear Thigh High Boots In 2023

“Thigh high boots (or cuisaardes, which include thigh boots, top boots, hip-boots and waders)… are long boots that fully or partly cover the knee.” 

“Thigh-high boots, are known as thigh-lenght boots or simply thigh boots, are boot that extend above the knees to at least mid-thigh. Other terms include over-the-knee boots… OTK boots.”

Well I think you have a good enough explanation as to what are thigh high boot, now let’s get to know how you should style these thigh high boots to your liking. 

What Are The Dos And Donts Of Wearing Thigh High Boots? 

When you are buying thigh high boots, there are certain things that you should and should not do, so here is a rundown of the dos and don’ts. 


  • You should try out block heels over stilettos. 
  • It is better to show some skin between your outfit’s bottom and the boots’ top.
  • To go the classic route, try wearing black leggings and black boots.
  • 2023 is the year for wearing slouchy boots.
  • To feel a bit more comfortable, you should wear thigh high boots, since they are warm and comfortable. 


  • If you are wearing a skirt or a dress with a shorter hemline, pair it with ankle boots or heels. 
  • With a midi skirt, you should wear thigh high boots as well. 
  • Round-toe boots are back again. 

Different Ways To Style Thigh High Boots

So let’s check out a few of the gorgeous pairings with thigh high boots that you can create a gorgeous outfit with. So keep on scrolling to find out. 

1. OTK + Button-Down Dress

OTK + Button-Down Dress

One of the classiest ways of pairing thigh high boot is with a simple button-down dress. The color of the dress is not a big deal as long as it is cute. The look gives a very feminine look to you as a whole. 

With the thigh high boots, the boot are gonna look even better and cuter. With a cute button down dress, you can try any type of thigh high boot you want, like suede or even leather boot. 

2. Monochromatic Winter Outfit Idea

When it comes to wearing boots, I am all for wearing a monochromatic look with a nude undertone to it. The trend of wearing nude or neutral colors has been strong ever since 2022. 

So if you add monochromatic colors to the mix, then you are surely gonna stand out from the crowd. 

If you buy gorgeous black thigh high boots, then you can easily pair them with a black dress, pants, or skirt of similar monochromatic colors. You can play with the different shades of the color as well; that might go great with black boots.

3. Gingham Dress + OTK Boots Outfit

Gingham Dress + OTK Boots Outfit

During the fall, gingham dresses are usually out, and thigh high boots go really well with them. If you want, you can also add a belt to the dress to cinch the waist; that way, the dress won’t look slouchy on you.

In the fall or winter months, it is almost a staple to wear gingham dresses along with thigh high boot to protect yourself from the harsh winter chills. 

To accessorize with the dress, you can wear a chunky belt, as I said, and jewelry to go with the dress you are wearing. 

4. Thigh High Boots + Sweater Dress

Just like with a gingham dress, you can wear gorgeous thigh high boot with a sweater dress. Pairing a sweater dress with thigh high boots are the best outfit you can wear during winter. That you are both warm and fashionable at the same time. 

Just like with a gingham dress, you can either match the color of the boot, or you can wear a thigh high boot with contrasting colors entirely. 

5. Plaid Skirt + Boots Outfit

Plaid Skirt + Boots Outfit

I think by now you can very well understand the type of dresses or outfits that go great with gorgeous thigh high boot. With skirts, if you wear thigh high boot, then the whole look is quite flirty and cute. 

The whole plaid skirt and corset top situation screams Fall and Winter months and can look better than maybe red thigh high boots or classic black thigh high boots. This is a fashion trend that is never going out of fashion, at least in the next few years.

This outfit can also be a cute look for a date night, so for a date night in the fall, you don’t have to think twice about the outfit that you are wearing. 

6. Corduroy Skirt + Boots

When it comes to skirts, you can practically pair thigh high boot with any type of skirt, whether it’s leather, plaid, or even corduroy skirts. No matter the occasion, you can always wear a corduroy skirt with thigh high boots. 

It is like a fall or winter essential at this point. It is a look that is hard to beat during the winter months. And to play with the colors even further, you can always try to mix and match the colors black and brown. 

7. A Simple Dress With Thigh High Boots

There are certain occasions when all you want to do is to make your thigh high boots the statement piece in your whole outfit. It is possible that you bought pink thigh high boot, then with that, wear a neutral-colored dress. 

The color shades such as beige, cream, or even pastel shades are perfect to wear with pink thigh high boot. In this outfit, the statement piece is the pink boots and not the dress itself. 

8. Thigh High Boots For The Holiday 

Well, during the holidays, the color that goes great is the color red. So if you are feeling fun and festive, then wear red thigh high boot with a cute fringe or leather skirt. 

But if you think the color red is a bit too bold for your choice, then you can always wear a great pair of white thigh high boots or the classic black as well. 

9. Classic Trench + Boots

Classic Trench + Boots

The classic trench coat and thigh high boot are a match made in fashion heaven. You can never go wrong with such an iconic pairing. 

Whether you put on a brown trench coat or a black trench coat, a pair of thigh high boots are the quintessential match. The look is quite chic with a certain French vibe to it; you just have to add a pair of dark sunglasses. 

10. Belted Tweed Dress Outfit

If you are going for a classy and elegant look, then what you should be wearing is a tweed dress with a belt to cinch the waistline. 

And to complete the look, you can wear the most gorgeous thigh high boots in any color you want. But normally tweed jackets or dresses look great with black thigh high boot as they are as classic as the tweed. 

Wrapping Up!

When you are looking forward to buying thigh high boot, there are a few things that you should keep in mind. The first is to decide on the material you want your boots to be. 

Secondly, consider the number of times you wanna wear the boots that you are buying. And lastly, be very careful while wearing them, since they are thigh high boots. So if you follow these suggestions, then your boot-buying experience will be much easier.

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