8 Over-The-Knee Boots To Try This Winter + Some Tips

Woman Wearing Over The Knee Boots

Ladies, let’s talk shoes!

Now that Autumn is here, sandals just don’t cut it anymore. Not only have the temperatures dropped, but it’s raining everywhere, to the point that even high heels would not be a smart choice. As such, it is the perfect season for boots.

There are several types of boots you can choose from, with booties being the most popular during this time. However, there is one type that is often overlooked: the thigh-high boots.

While to some this might be surprising, most women avoid wearing them. It is mostly the connotation, especially after Pretty Woman was released. They sort of turned into a statement of non-sophisticated women, which is unfair as they are not only sexy but very elegant, too.

Another reason is also the mismatch between seeing a model wear them and actually wearing them. When you put them on, some designs are uncomfortable and others just plain refuse to stay in place, looking nothing like what you hoped they would.

But, for those of you who love these boots and those curious to try them on, luckily they are always in style and the designs are plentiful. You can wear them for a casual outing or in the workplace, looking classy and elegant.

For today’s piece, we have selected 8 gorgeous designs that we are sure you will love. Also, to help you make the right choice and not have to stress over wearing over-the-knee boots, there will be tips included after we take a look at our choices.

* Keep in mind that: The availability, colors and sizes of the products below may change at any time. Also please check the products features on the various shops before buying. The product images shown are for illustration purposes only.

Stuart Weitzman Over The Knee Boot 5050

Stuart Weitzman Over The Knee Boot 5050

Image: pinterest.com


Let’s start with Stuart Weitzman’s 5050 boots.

They are made of leather and have a rubber sole, which is designed for comfort and it is also anti-slip due to the bottom ridges.

These are low-heel boots, with a heel that measures about 1″ (2.5 cm) high, making the boots suitable for everyday wear, especially if you will be walking around during the day.

The shaft measures approximately 21″ (53 cm) and the back fabric is elasticized, to make it easier putting them on, as well as during movement.

The opening is about 14″ (35.5 cm) and they are slip-on boots, without laces or zippers.

They are available in 10 color variations of suede and shine: Black, Slade, Cola, Nice, Nice blue, Topo and Bordeaux.

You might also like: 8 Beautiful Monicoco Dress Shoes

Dream Pairs Colby Casual High Boots

Dream Pairs Colby Casual High Boots

Image: pinterest.com


This next pair of boots and the one after it, are both by Dream Pairs. The first design is Colby, in a beautiful slouchy design, made with synthetic leather on the outside and faux fur lining on the inside, for comfort and warmth.

The outer sole is made of rubber, measuring around 0.5″ (1.2 cm) high, very comfortable to walk around in. The insole is cushioned for better support and to reduce fatigue when wearing these boots.

They have a round toe and the calves can be adjusted to size, which means that these boots are suitable for wide calves.

To put them on, there are zippers on the inner side of the boots, along with back laces and a stylish strap and buckle close in the back.

There are 9 colors to choose from, with both suede and shine options: Brown, Grey, Black, Camel and Khaki.

Read also: Best Women’s Dress Shoes? Try These 8 Ideas

Dream Pairs Leggy Stretchy Faux Suede Boots

Dream Pairs Leggy Stretchy Faux Suede Boots

Image: dreampairshoes.com


The second design is called Leggy, a lovely design with a hidden wedge heel, that measures about 2.75″ (7 cm) and with a 0.25″ (6 mm) platform.

These are elegant boots that can be worn in different occasions and come in a very classy look. They go great with jeans, especially.

The material is faux suede leather, which is stretchy, making the boots easier to wear and the legs appear slimmer. There is a short zipper on the side to help when putting the boots on, as well as a drawcord in the opening for a better fit.

The shaft is 22″ (55.8 cm) high and with an opening of about 15″ (38 cm) around. Leggy comes in 6 colors: Blue, Brown, Grey, Khaki, Black and Wine.

You might also like: 9 Tips To Make Your Legs Look Longer

Kaitlyn Pan Microsuede Flat Over The Knee Boots

Kaitlyn Pan Microsuede Flat Over The Knee Boots

Image: pinterest.com

(Not Available)

By Kaitlyn Pan, these microsuede boots are perfect for a casual look and everyday wear.

The outer lining of microsuede is synthetic, while the inner lining is made of genuine lamb skin. The reason for this is the breathability of leather and its ability to adapt better to different feet types and sizes.

These are slip-on boots, with a ridged outer sole that has a 1″ (2.5 cm) heel. The shaft is 23″ (59 cm) high and has a opening of about 13.4″ (34 cm), which can be stretched up to 15″ (39 cm).

They come with a narrow round toe and a color-matching drawcord in the top opening, for adjustment. You can purchase these boots in 5 colors: Black, Army green, Burgundy red, Grey and Taupe.

Ollio Over The Knee Zip Up Long Boots

Ollio Over The Knee Zip Up Long Boots

Image: pinterest.com


Another stretchable boot, this design is by Ollio. They have a 21″ (53 cm) shaft with a 15.7″ (39.8 cm) opening and the heel measures 1″ (2.5 cm) high.

The material is faux leather in both suede and shine designs, very stretchable and comfortable to wear. There is a short zipper on the inner side of the boot, as well as a drawstring in the opening for better adjustment.

The toe is rounded and narrow and the outer sole is made of rubber. There are 8 options to choose from, while the colors are 6: Black, Taupe, Tan, Olive, Wine and Pewter metallic.

Beston GF59 Drawstring Tie Strech Boots

Beston GF59 Drawstring Tie Strech Boots

Image: shopbeston.com

(Not Available)

Continuing with another double selection, these two are by Beston. GF59 is the first pair in line and they come in a beautiful slim design, with a very high shaft.

The shaft is about 23.5″ (59.6 cm), making these boots suitable for short dresses and skirts. They come with fabric cords in the opening and short side zippers to help put them on more easily.

The material is faux suede and the heel measures about 1.25″ (3 cm). There is soft lining inside the boot and visible stitching on the outside, which go great with the design and the look of suede.

This pair comes in the colors: Black, Grey, Navy, Wine, Cognac, Taupe and Brown.

You might also like: The Best Flattering Skirts for Big Hips and Thighs

Beston FD97 Stretchy Over The Knee Boots

Beston FD97 Stretchy Over The Knee Boots

Image: shopbeston.com

(Not Available)

FD97 are also made of faux suede, with the shaft measuring 21″ (53 cm) in height. The heel is approximately 1.25″ (3 cm), making them suitable for both casual and workplace wear.

There is a short side zipper and drawstring in the opening for adjustment. These are not very stretchable boots, so it should be kept in mind when ordering, especially if you have thicker calves.

The toe is round and there are 4 colors to choose from: Olive, Black, Tan and Taupe.

Sam Edelman Bernadette Boots

(Not Available)

To end this selection with some attitude, Sam Edelman‘s Bernadette boot is the perfect choice. This sexy design is made of suede and comes in a stiletto type heel, with a pointy toe.

The heel measures about 4″ (10 cm) and the shaft is approximately 27″ (68.6 cm), making this design the highest in both heel and shaft.

The top opening is split in a V-shape, which widens it for a very carefree and daring look. To put them on, there is a short side zipper. You can pick your favorite color out of the 2 options provided: Black and Grey frost.

Some Tips For Purchasing Your Over-The-Knee Boots

As promised, now we will share some tips for your next thigh-high boots’ purchase. These will help you look and feel amazing while wearing these, sometimes tricky, stylish boots.

Material is key

While there are a limited number of material options when it comes to boots, if possible, opt for genuine leather. Leather is ideal as it adjusts with the size and shape of the feet and legs over time.

However, when it comes to thigh-high boots, you should look for elasticized shafts, in order to ensure that now only will they fit, but that you’ll be comfortable wearing them. This is especially important if you have wide or muscular calves.

Color selection

Unlike other boots, over-the-knee ones are a bit tricky to match with the rest of the outfit. They run the risk of looking too over the top and can make or break an entire look.

This is why, if you are going for a bold short dress or will be wearing fur and very extravagant tops, look into nude and soft shades, to make everything look stylish and well-put together.

Slouchy or tight

While design comes down to preference, it should be taken into consideration on several factors. For example:

  • Casual: For day-to-day wear, either design is fine, especially for low-heel boots. But if you are looking to not be as “out there”, a slouchy design will appear more laid-back and goes better with casual outfits.
  • Night out: Slim designs are the best option, especially if you want to look sensual and elegant. Opt for a stiletto heel, that way you will both feel and look sexy.
  • Work: When it comes to the workplace, it depends on the outfit required to be worn there, but as a general guideline, we’d recommend slouchy designs and preferably a low-heel as well. If you must wear a high heel, then go for block ones, rather than stiletto-style heels.

Play around

By this, we mean the way the top is worn. You do not have to wear them straight on! The fashion police won’t mind, trust us.

Fold them over or wear them lower, to make them appear slouchier, and just have fun wearing them.

Transform your look

If you are a jeans-and-sweater type of girl, slim thigh-high boots will transform your outfit from “simple” to “fashionista” levels in an instant. They will also make your legs appear longer and slimmer, especially when wearing skinny jeans.

And lastly, put on those boots and wear them proudly and boldly!

That’s it for this topic! We hope to see you in our next article! As a conclusion, here is a video about how to style over-the-knee boots:

HOW TO STYLE: Over The Knee Boots + LOOK BOOK

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