Autumn is around the corner and there’s isn’t a better time to bust out those over the knee boots for fall, than this. The colder months are too chilly for short boots, anyway. The aim of this style guide, is to keep your winters warm without losing your pizzazz. We admit that thigh high flat boots such as these, are not as Instagrammable as last year, but one can’t deny the unique style statement they make. Some of you believe that only long-legged ladies can rock over the knee boots but these shoe types are still considered as the hottest shoes in history.

The ‘hottest’ here is an expression and it’s also practically true since winters are here and what better than a pair of thigh high ladies flat boots.

No one is looking to spend most of their winters at home, wrapped up in blankets, avoiding thick clothing due to white ocean of snow outside. The answer is not thick clothing but the right outfit which also consists of over the knee boots.

Fortunately, you have a number of options available in the market, but unfortunately, not all of them can be in your wardrobe. Below, we will go through the necessity of thigh high boots in winters and how you can style them while keeping yourself warm this winter.

Winters- The Season of Thigh High Boots

Winters are harsh on fashion but winters are the time of parties and gatherings. It is certainly not easy to look stylish and stay warm at the same time. Most of the girls enjoy their Christmas Eve or New Year’s party under those multiple layers of clothing.

But this is why tall boots have been an easy solution during winters to grab attention while being warm as well. You can confidently walk in them on the snowy streets during holidays and enjoy time with friends without feeling cold.

Pick Quality Over Everything Else

Women’s thigh high boots are a statement piece. Messing around with the quality will hurt you later. These are one of the most stylish staples to have in your wardrobe but you do not buy tall boots every day. So, before thinking about whether to sport it with skirts or jeans, make this rare investment carefully. You should never go wrong with the voguish and classy thigh high boots.

Over the Knee Boots and Your Appearance

You can discover multitudes of colors and models available in the market of thigh high boots but there’s always a pair that will win your heart. Sporting knee-high boots will also make your calves look slimmer.

Most of the ladies know that tall boots have a seductive enchantment over guys which is also a reason to wear them gracefully. OTKs are also highly adaptive since you can wear them to places where you want to look good but not daringly pretty such as an evening meal with family or friends, your office, and even at church. You can match OTKs with anything in your wardrobe.

Contrary to popular belief, tall boots are quite versatile. You can pair these long boots with lengthier as well as short skirts. While the lengthy skirts will give you an overall passionate look to go as office attire, the short skirt with thigh high boots will give that sensual yet stylish look. They can also fall perfectly with other dresses and jeans. You can wear them to work as well as to dates because their coziness and style make them the perfect footwear in the Winters.

How to Look Smart and Stylish in Thigh High Boots

Confidence is the key to look smart and stylish in a pair of over the knees shoes. Without confidence, you will look dull even in your favourite pair.

Whether you are headed to your office or going on a date, the only way to style your thigh high shoes is with confidence.

Thigh High Socks

Before you put your feet in the over the knee boots, you can check the look with the combo of long boots and tights.

Layer Them or Go Monochromatic

Your thigh highs can play well with layers. You can wear skinnies, tights, or leggings with your boots to have perfect layering and add your statement items. Sporting a monochromatic appearance will draw more attention to the overall look rather than just boots.

Short and Long Combos

Women thigh high boots go well with against long winter coats as well as short skirts. You can wear short skirts and thigh high flat boots with very less skin left to be seen. This will give you a bold look while also keeping you warm.

Go For Classic Materials

You may want to have a similar vibe to Rihanna with denim thigh high boots but experimenting with unusual colors and materials may go wrong. Instead, always go for grey or black leather or suede. Also, make sure that you buy a perfectly fitting suede.

Outfits That Look Good With Long Boots

A wide range of outfits goes perfectly with thigh high boots. You can incorporate these beautiful boots into your fashion in different ways. Short skirts are the first priority to go with tall boots. They also look fashionable and attractive with skinny jeans or a midi dress. However, there are a few things to avoid while rocking your new knee-high shoes.

Anything too flashy can ruin the whole look. This will direct all the attention to your shoes instead of the whole outfit in general. Try to sport a classy appearance to keep everything neutral. You can mix and match the shades of the boots with your clothes while keeping it minimal whenever going somewhere out.

Dos and Don’ts Of Wearing Long Boots


  • Go for an outfit at least covered to some extent such as midi or maxi length, high neckline, etc. This is a great way to look sophisticated while not overdoing things.
  • Use a hemline to cover the top of your shoes. Midi-length should be your first choice with thigh high boots.
  • Carry a super bold look by draping a coat over your shoulder.


  • Let the skin between your boots and skirt hemline exceed 12cms.
  • Wear dull colours, shiny details, and let your shoes overshadow the rest of the outfit.
  • Wear boots too loose or too tight. The best pair is the one that fits perfectly so buy one even if you have to compromise with the material.

Sporting dresses at this time of the year is challenging but chic as well since some dresses are meant for wintertime.

Girls usually avoid wearing dresses in winter since it’s easy to pull some jeans-sweater combo rather than some fancy dresses that never help in winters. However, thigh high boots put sense to everything.

Whether you have a wrap dress or you are planning to style one for work or whether you would like to go for that ruffled look that you love – over the knee boots can make you stylish as well as cosy at the same time in anything.

Like short dresses? They can be the reason for the cold you get in winter. Usually, you should avoid short dresses in winters but they can work in music festivals or other parties. In that case, your hemlines deserve all the attention because as soon as hemlines or both boots and dress touch, your step into a sophisticated look. You can wear short dresses with thigh high boots to family dinners, business meetings, and even your office.

How to Wear Thigh High Boots to Work

Imagine a man-inspired look of a tailored blazer with a striped blouse and jeans. The only thing that will make it a woman-inspired look is knee-high ladies flat boots. They will complete an appropriate and bold look for the office. You can also add details such as a red clutch or a scarf.

We understand that over the knee boots can be intimidating but you shouldn’t be afraid to style them to office. However, there are certain things to take care of before wearing them to work.

If a skirt is your first choice for work, make sure to get a midi-length skirt. You can opt for a basic look and enhance your appearance by adding details. As mentioned earlier, a classic and sophisticated look can work perfectly in the office.

Assuming that you are allowed to wear jeans at your workplace, you can rock jeans-blazer fusion with a unique and impressive detail – thigh high flat boots. Thigh highs come out totally different and give an entirely new look.

If you’re not someone who likes experimenting with colors, prints, or materials, go for something casual. Black is considered the best idea when you have limited choices in colors. Remember to add a statement detail such as a pair of earrings or a stylish bag.


Winter is the season of shoes. However, even after being great at protecting your feet from cold, thigh high boots were never considered an everyday footwear. The written piece explore the reasons why thigh high or over the knee or knee high boots can be great for different occasions and places in the wintertime.

About the Author Brian

Hello, I'm Cindy. I’m a super duper mega hiking enthusiast, with a love for everything that has to do with outdoors, hiking, gear, footwear and more.

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