8 Ways to Wear Thigh High Boots

I have mentioned several times on this blog how much I envy women who are able to wear thigh high boots so effortlessly during the cooler months. As a member of the very thick calf committee, there are so few thigh and knee-high boots in the world that can fit my legs and that’s why I tend to stick to ankle or calf boots most of the time.

I know must of us can remember the iconic scene from the movie Pretty Woman where Julia Roberts is sitting on a bench waiting for the bus in her short skirt and thigh high boots. Those black leather boots by Vivian Ward were definitely a fashion moment that most fashionistas would never forget.

Now although Julia Roberts was wearing hers while on duty as a prostitute, there is no reason why thigh high boots have to be considered trashy. I know a lot of people give tall boots a bad rep but in today’s post I want to show you how you can create chic thigh-high boot outfits that would keep you warm yet very stylish.

You don’t have to save them for that one time a year you pair them with a mini leather skirt and a cop hat for Halloween. Over-the-knee boots (also known as otk boots) are actually a great option of boots to choose if you want to take your Fall looks to the next level.

Before we take off into the different ways to wear thigh high boots, I would like to share some great options of tall boots that you can wear to create great thigh high bot looks for different occasions.

*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.

i) Gianvitto Rosso thigh highs

If you’re on the hunt for some luxury over-the-knee boots, then these Gianvitto Rossi black thigh high boots should be in your shopping cart. They would really compliment any edgy look you may be trying to create and the focus would definitely be on your legs. I love that the boots are composed of 16% elastane, meaning they have some great stretch.

 Saks Fifth Ave is my go-to destination for all things luxury as you have all of the luxury brands available in one place. G. Rossi has become quite the household name in the luxury shoe department thanks to their unique and sleek designs.

ii) If you can’t afford to drop thousands on a pair of luxury boots just yet, Steve Madden may be your best option. The brand offers pretty comfortable high boot options at affordable prices and you can find them on DSW. I like to visit DSW because they tend to have stock available when shoes are sold out on the Steve Madden website. These Steve Madden OTK boots feature a sleek faux leather and a flatform heel.

Thigh high boots don’t necessarily have to have high heels and by going for a flat boot, you can create more looks for everyday wear.

Another reason to love DSW is the fact that they have an entire section of boots dedicated to women with wide calves. You can check out a great list of options for tall boots for women with wider calves HERE.

iii) Never forget to check out Nordstrom if you’re on the hunt for a new pair of thigh high boots. Jeffrey Campbell has the Parisah boots which are suede thigh-high boots that come in different neutral colors, perfect for the Fall. They’re a great affordable option to go with if you want a comfortable block heel versus a stiletto heel which is harder to walk in for extended periods of time.

This over the knee boot would look great styled with a trench coat or oversize sweater. I personally prefer the brown color the most and in case you’re wondering how to style them, just think of how you would style them if they were black boots.

iv) If the prices above are still way out of your budget, then I present to you ASOS’s options for over the knee boots. You can find thigh high boots for under $30 if you’re really just looking for cheap thigh-highs. I cannot vouch for the quality of boot you would be getting (although they do have a lot of 4 star reviews) but it’s great to know this option is out there. I would get these OTK block heel boots for example if I were shopping for a Halloween costume and did not want to spend much.

Those are my favorite websites to check out for taller boots and now that we’ve gotten that out of the way, let’s discuss styling these pretty boots to create stylish and classy looks that would look great on any body type.

1) Thigh high boots with an oversized sweater

The winter months call for cozy outfits and this is one that is just as chic as it is cozy. Pair your over-the-knee-boots with a chunky sweater and a pair of leggings to serve up some major fall or winter fashion or go without the leggings if it’s nice outside. You could also add a wide brimmed hat to this chic look to make it even more eye-catching. I love how this look requires few pieces to bring it together and yet is a very memorable one.

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2) Thigh highs and skinny jeans

Skinny jeans are the best choice of jeans to pair with thigh high boots because they’re probably the only ones that can fit. I can’t imagine trying to stuff a wide-legged jean into a thigh high boot. All of that fabric would lead to some serious bunching all over the calf, making your look a frumpy one.

Add a cropped sweater to a pair of skinny jeans and then throw on a pair of thigh high boots to create a bomb date night look which could also be worn for a night out with the girls in the colder weather.

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If it’s not too cold outside, try pairing your fitted tops with some black skinny jeans and a leather jacket to serve up a sassy thigh high outfit. Choose a heeled boot if you’re headed somewhere fancy and want to give your derrière a nice lift.

3) Thigh highs and shorts

Who says over the knee boots had to be reserved for winter fashion? You can create a chic look worthy of a Beyoncé concert in the summer with a pair of these boots. Wear an off-shoulder tee or sweater and pair it with a pair of denim shorts.

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The top of the boots could hit right where your shorts end and make it look like you’re wearing a pair of jeans if you wish. You could also decide to pair a tank top or crop top with the shorts and throw on a denim jacket to create a concert look to turn heads.

4) Thigh highs and skirts

The best way to pair thigh high boots with skirts is to choose skirts that hit right where your boots end. This would prevent your outfit from looking trashy. An A-line skirt with a simple blouse could be paired with over the knee boots to create a chic look you could wear to the office. During the colder months, replace the blouse with a sweater and you’ve got yourself an office-appropriate fall look.

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If your skirt is on the shorter side and you don’t want your thighs to show, add a pair of black leggings to the mix. My favorite outerwear to complete this look is a trench coat in a neutral color. For a more casual look, opt for a shorter pleated skirt which you could pair with a t-shirt or a tank top. This look works great for happy hour with the girls.

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5) Thigh highs and dresses

Whether you’re opting for a midi dress or shirt dresses, pairing them with thigh high boots is the easiest way to amp the sex appeal in your personal style. I recently wrote a post on what shoes to wear with a shirt dress and a pair of boots was definitely on the list. The shorter the dress, the higher the boots, in my opinion. If you’re feeling bold, you could choose a pair of tall boots in either a bright color or in animal print.

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A classic shirt-dress with a pair of thigh high boots would look great with a structured blazer on top. During the winter, create a chic look by pairing your oversized sweater dresses with a pair of leather leggings and topping it off with some OTK suede boots. You could add a warm coat to your overall look and you’re ready for a holiday party or the office.

And there we have it; 5 simple thigh high boots outfits that will not have you looking trashy. If your body type is more curvy, just be careful when selecting skirts to wear with your boots because out curves tend to make our skirts ride higher up. It might be safe to go with skirts that are 2 or 3 inches longer than our typical mini skirts to be safe.

I hope that you have found this list hopeful and would try out at least one of these looks the next time you whip out the thigh high boots. Remember to check out the wide calf section of DSW for thigh high boots for women with large calves. I’m a part of that team and can understand the frustration when searching for boots that would fit us.

You may also want to check out my post on different ways to style black Ugg boots.

For ideas on how to style your tall boots with dresses, check out my post: Top 7 dresses to wear with thigh high boots.

Until the next post,