Your Complete Guide To Buying and Styling Over The Knee Boots

How To Wear Over The Knee Boots

Over the knee boots have become a huge wardrobe staple and long gone are the days of associating them with Pretty Woman’s thigh-high hooker heel. Even still, they can be an intimidating item to wear. They aren’t exactly a boot that you just “throw on” and head out the door. In this post, I’m giving you all info you need to know about over the knee boots including which ones to buy, how to style them, what works, and what doesn’t.

What To Know Before Buying Over The Knee Boots

The first thing to know is about over the knee boots are that they have many different names. You may see them advertised as thigh-high boots, top-boots, hip boots, or just OTK boots for short.  Also like all other shoes, not all OTK boots are created equal. They can be incredibly flattering, elongate your legs (yes! even for your petite girls), and are an easy substitute for heels or pumps during the colder months. However, it takes finding the right pair in order to achieve this elevated look. 

Are Over The Knee Boots Still In Style For 2021?

Over the knee boots most likely arent going anywhere soon. They have actually been around since the late 1800s where they were a popular men’s riding boot. They became super popular in women fashion during the early 1960s and have been trending since. Since 2015 they have been one of the top-selling boots styles during the winter months, and I don’t predict them leaving the runways just yet. 

Your Guide To Buying Over The Knee Boots

How To Wear Over The Knee Boots

What To Look For When Shopping For Over The Knee Boots

Are they comfortable? With pairs of shoes, you want to know how long  you will be able to wear them for and if you will be cursing at yourself by the end of the night ( ladies don’t lie – we’ve all been there.) This can be tricky seeing as you can walk a mile around the store before purchasing. Make sure to take a long stroll through the aisle though and if there is no apparent rubbing or throbbing you are probably good to go. Of course, I am biased here, but use bloggers are a resource! They already own them, so don’t be afraid to reach out and ask them what they think! Also, remember to consider heel length as a comfort factor. Heel size will have a huge part in this.

Material –  Do you want real leather or suede? Personally, I love suede boots. I can’t get enough of them and love the elegant look they give off.

Do they stay up? This is by far the biggest complaint I hear about OTK boots. The shaft will not stay up. If your keep sliding down then you DO NOT have the right pair of boots! In fact, I wrote a whole post on an amazing pair that DO stay up. 

Shaft Height –  Are you looking for a pair that this mid-thigh or just over your knee? Know that sitting or bending down should still be comfortable and if you are having a difficult time then I suggest finding another pair of boots. 

Different Over The Knee Boot Styles

Heeled – Great for a dressy occasion like a party, date night, girls night out, or for anyone who just wants a little height. 

Flat – Keep it more casual with flat over the knee boots. Perfect for everyday wear.

Mid Thigh – Amazing for elongating your legs!  

Just  Over The Knee –  Good option for people who struggle with shafts that constantly fall down or Petites.

Best Affordable Over The Knee Boots

This is tricky because everyone has a different idea of what “affordable” means. We’re going to say under $175 for the sake of this post. Also, I am going to link some that are on major sale or a few pairs that always have a discount code. 

1.Goodnight Macaroon–  I personally think these are THE BEST for your money. There is a reason why they are so popular among bloggers. They stay up, come in 3 different colors, and they always go on sale. They retail for $159, but I know they go on sale for as low as $88. If you want to keep up with the best sales be sure to follow my LIKEtoKNOWit page. There is also now a heeled over the knee version with ties. I personally have not tried them so I have no idea if they are as good as the original. 

2.Steve Madden Tava Over The Knee Boot These retail for $135.  They have great reviews, but the only problem is that they sell out quickly. They come in black and a tan color. 

3.Marc Fisher LTD – These are past the $175 price point and normally retail for $240. However, they always go on sale and they are incredibly good quality boots. The LTD comes in three different styles this year including the  Comara, Charlote, and Onyse.

Best Over The Knee Boots To Splurge On

Stuart Weitzman – This legendary brand is the go-to if you are looking to splurge on over the knee boots. They come with the highest praise and are a classic style that has been around for years. Stuart Weitzman’s most popular style for OTK boots is the Highstreet (formally Highland), City Knee, and the 5050 Boots.

Ways To Style Over The Knee Boots

1. Skinny Jeans

Pairing jeans with boots is by far the most casual option but also my favorite. I love pulling on a loose sweater, dark skinnies, and then my OTK boots.

Do – Make sure to pair your OTK with a tight pair of skinny jeans and form to your legs. I also suggest a pair of high waist jeans that will make your legs look even longer plus I am a sucker for a front tuck. Don’t be afraid though of a long loose sweater. It will balance out your slim leg line.

Don’t – Stay away from straight leg jeans or any jeans that will bunch under your boots.

2. Skirts

I love pairing skirts with over the knee boots. However, this is the area is where we enter Pretty Woman territory, but I have few tips below on how to avoid that.

Do – Make sure that your skirt hem hits ABOVE your boots.

Don’tDon’t wear a tight-fitting mini skirt. Instead chose a skirt that has an A-line style or fit and flare. 

3. Dress

Wearing a dress with over the knee boots is similar to wearing a skirt. You want to make sure there is a visual difference between the hem of your dress and the boots. Feel free to wear tights under your dress or skirt! Wearing midi skirts or dresses with OTK boots has become popular and in that case, you don’t need to worry about hem-lines. 


There is really one simple rule when wearing over the knee boots with leggings and that is to make sure your bottom is covered! Chose a tunic, blouse, or sweater that fully covers your bottoms to avoid an overly revealing outfit. Feel free to layer a long tunic blouse with a cardigan or an oversized chambray shirt under a sweater, just make sure your top isn’t too short.

How To Wear Over The Knee Boots

Over The Knee Boots Tips & FAQ’s

How To Put On Over The Knee Boots 

The best way to put over the knee boots on is to roll the material down as far it will go – much like how you would put on thick winter socks. If there is a zipper at the bottom make sure it is unzipped and that your jeans or socks are not bunched at the bottoms. Once your foot is in, roll the boot back up over your leg and knee and adjust. 

Will OTK Boots Make Me Look Shorter? 

NO! If anything they should elongate your legs and make you appear to be taller! Especially in pictures 😉

I hope that I have answered all of your questions about buying, styling, and wearing OTK boots. If you have any other questions, leave them in the comments below!

All My Love,

Michelle Marie



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  1. 4.7.21
    Jami said:

    Will you recommend the mid thigh boots you mentioned?

    • 5.6.21
      michelle marie said:

      Hi Jami! Any boots that I linked, I have done a ton of research into and recommend! Overall, if you are looking for a mid-length/ thigh-high boot, I recommend the Goodnight Macaroon boots. I have worn them for years and they are still going strong!