Top 7 Dresses to Wear With Thigh High Boots
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  • Writer's pictureBrenda

Top 7 Dresses to Wear With Thigh High Boots

Updated: Feb 22

When it comes to boots, thigh high boots are the sexiest option. There’s just something about a shoe reaching al the way up to your thighs that makes any outfit instantly more sexy. I think it also has to do with the fact that most outfits paired with over-the-knee boots tend to be shorter, as typically the wearer wants to show off their tall boots.

I have covered different ways to style a pair of thigh-high boots several times on this blog. Most recently, on my post: 8 ways to wear thigh-high boots, I covered the different ways to create a high boots outfit without looking trashy. This is because a lot of people associate these boots with overly sexualized outfits. Perhaps it’s because of pop culture and movies such as Pretty Woman where Julia Roberts plays a lady of the night and is seen in them.


This does not have to be the case. Conclusions such as those cannot be made based off a woman’s choice of footwear. I for one would love to be able to create chic outfits with a pair of knee boots or higher but cannot unfortunately. You see, I have been blessed with very wide calves and so finding boots that go past my calves has always proven to be a challenge. I envy those of you who are able to rock these long boots with ease.

In today’s blog post, I would be focusing on showing you outfit ideas you can come up with when pairing your OTK boots with dresses. You can create both dressy looks as well as more casual ones with a pair of tall boots. I would be showing you how to style different types of dresses to create looks you can wear across different seasons.

Boots available HERE

I think it’s important that I start off by sharing some great options of thigh high boots and where you can purchase them. If you’re looking for a pair to add to your wardrobe, or seeking to buy your first pair of tall boots, then you would want to check these out. You would be able to create many stylish outfits during the Fall and Winter with these options.

*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

Where to buy thigh-high boots

i) DSW

To know me is to know how much I love me some DSW. Their range of footwear is second to none and so I always make sure to include them on every post involving footwear. I really appreciate how they have an entire section dedicated to women with wide calves, like myself. You can easily find any type of boot to pair with different items in your wardrobe.

When it comes to thigh-high boots, you must start with a pair of classic black thigh-high boots. If you can only afford to own one pair of tall boots, you must own THESE. You could pair them with sweater dresses, mini skirt and even short shorts to create several chic looks. The block heel is low enough so that these boots could be part of your everyday wear.

ii) Michael Kors

You probably were not expecting to see this name on the list, but Michael Kors has proven to deliver from very stylish and comfortable OTK boots. During their end of year sales, you can grab a pair at 60% off the original price. Although their selection of tall boots may be very limited compared to other websites, what they do offer are trendy luxury boots.

THESE suede boots are so stylish and feature an eye-catching gold heel. You could wear them for more formal occasions by styling them with a knee-length dress. The very low heel makes them very easy to walk in as well.

If you are looking for leather knee-high boots with a small heel, check out THIS PAIR.

iii) Nordstrom

Nordrstrom is another platform that offers a nice range of options when it comes to tall boots. They have the extremely tall boots such as THESE Azalea Wang thigh-highs that would be a great option to create an edgy look with. Several other brands are represented in this department on their website but none of them stand out like Jeffrey Campbell.

Jeffrey Campbell shoes are known for their uniqueness and comfort and THESE Compass thigh high booties hit all the marks. The heel is so unique and as per the comments, surprisingly comfortable. If you are looking to stand out in a pair of thigh-high boots, these are your best option.

iv) Shein

Shein brings you tall boots that range in price from as low as $30 to over $100. You could easily create everyday looks with many of their over-the-knee boots as most of them are black and feature a sensible heel height. If you’re looking to switch things up from your typical black leather boots, try out a pair of slouchy boots such as THESE brown ones.

Pair them with jeans, midi skirts or midi dresses to create cute outfits you could wear to work or for other activities. I find that the look of a slouchy boot is less formal and so I suggest you stick to wearing them for casual events.

If you’re feeling extra daring, try a pair of neon thigh high boots LIKE THESE.

v) Steve Madden

Steve Madden is synonymous with trendy footwear. They’ve managed to combine stylish shoes with pretty affordable prices. Their tall boots come in a wide range of colors, prints and styles and so it makes sense they’re on this list. Their Vava Rose patent boots may not necessarily be winter boots but they would definitely be attention-grabbing.

I can see them being paired with a mini skirt and a leather jacket for a stylish look you could wear to a concert. Another great way to style them would be with a patent mini skirt in a different color.

Now that you have a good idea of where you can find a good pair of thigh-high boots, let’s talk about the best dresses to pair them with. You can create chic outfits for both the winter months as well as warmer weather with a pair of OTK boots and a dress. It all depends on your choice of dress and how you style it.

The best dresses to wear with thigh high boots

1) Mini dresses

Short dresses are probably the most popular choice of dress style to pair with over the knee boots. This is because the top of the boots hit right where the dress ends, leaving a little bit of your thigh on display. This adds just the right amount of sexiness to your outfit. Of course, you can always avoid this by adding a pair of black tights underneath your dress.

Get the look HERE

Create an edgy look by pairing a mini dress with a pair of chunky tall boots and a black leather jacket. This is the perfect outfit for a rock concert.

2) Sweater dresses

Pairing a stylish sweater dress with a pair of sleek thigh-high boots is a great way of creating a chic look you could wear to more formal events. You could wear a fancy sweater dress and OTK boots to special occasions such as a winter wedding or an office party.

Get the look HERE

For a casual look, try pairing your tall boots with an oversized sweater, worn as a dress. Add a pair of black tights for extra warmth and you’ve got yourself a cute Fall outfit. This is an everyday look you could wear to class or the grocery store.

3) Little black dress

Instead of going for your regular high heels, try pairing your LBD with a pair of thigh high boots next time. This would make your black dress outfit more interesting and would also keep you warmer during the colder months. You could add a long coat on top and accessorize with a statement piece to create a look worthy of a gala event. You could even a full black outfit by opting for black leather boots and a black purse.

Image source here

4) Shirt dresses

Shirt dresses alone can be pretty simple and basic. Pairing them with thigh high boots is a great idea if you’re looking to make your shirt dress outfit more bold. A high low short dress would be the perfect choice as you would able to show off more of your boot. Add a skinny belt around your waist to create more of an hourglass figure.

Image source here

5) Skater dresses

A fit and flare skater dress is one of those cute dresses that looks flattering on any body type. One of my favorite ways to style them is with a pair of tall black boots. You can create many chic outfits by pairing your short and log-sleeved skater dress with a pair of really tall boots. This is a cute date night look you could wear with a pair of tights if it’s cold outside.

Get the look HERE

6) Oversized t-shirt

If you are looking for casual outfits to put together with your thigh-high boots, it doesn’t get better than this. A classic t-shirt dress could be worn with a pair of short denim shorts underneath (or not) to create a sexy yet laid-back outfit. This is the perfect choice of outfit to wear to a summer concert. You could also slip a pair of fish net stocking underneath for some added sensuality.

Image source here

7) Knee-length dresses

The purpose of wearing tall boots is to have the boots (and your legs) on display. That’s why knee dresses are as long as it gets when it comes to styling OTK boots with a dress. If you’re looking to cover as much leg when wearing your thigh-high boots, this is one of my favorite ways. Add a trench coat to your outfit if you’re headed for a professional event or a cocktail party.

Image source here

You could even pair one of your summer dresses with your thigh high boots to transition it from warm weather to colder weather. Floral dresses wok nicely with tall boots and you could play around with boots and cute dresses in different colors. Apply these same tips when styling your tall boots with midi skirts and oversized chunky sweaters.

Now you have a great idea of the different types of dresses you can pair with thigh high boots. You most likely already own most of the dresses mentioned. All that’s left is to begin pairing them with your tall boots for different occasions. You can create casual outfits as well as dressy ones with OTK boots and they don’t have to be trashy.

If you are interested in different ways to style a pair of ankle boots, check out my post 10 ways to wear flat ankle boots with anything.

Looking for ways to wear tall boots with everything in your wardrobe? Check out my post: How to wear tall boots with different outfits.

Until the next post,



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