How to Style Thigh High Boots: Outfit Ideas and Tips

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It’s no secret that over-the-knee boots (also known as thigh-high boots) are among the trickiest shoes to wear.

To some, they’re the kind to stay away from. Others love them too much and wear them with little care, so they look trashy.

Heidi Klum rocking sexy thigh high boots with skinny jeansHeidi Klum rocking sexy thigh-high boots with skinny jeans (Credit: Instar / WENN)

We’ve all seen the 1990 American romantic comedy film Pretty Woman. And the image of Julia Roberts in her micro-mini skirt and super-shiny over-the-knee boots is probably keeping most of the women on this planet from trying on that extra “tall order.”

Luckily, it’s not difficult to wear knee-high boots without looking trashy or like you’re wearing a costume.

A young red-haired woman dressed in winter fashion with a warm coat, scarf, and over-the-knee bootsA young red-haired woman dressed in winter fashion with a warm coat, scarf, and over-the-knee boots (Credit: Hilbrand Bos / Shutterstock)

While thigh-high boots are considered a fashion risk, they are also head-turningly sexy. If you wear them right (that is, in a tasteful manner), the rewards are close to priceless.

Remember that these boots are already considered quite a statement, so you really do not need to over-accessorize or add a lot of extras to your outfit.

Julia Roberts gave over-the-knee boots a trashy image as the free-spirited Hollywood prostitute Vivian Ward in the 1990 American romantic comedy film Pretty WomanJulia Roberts gave over-the-knee boots a trashy image as the free-spirited Hollywood prostitute Vivian Ward in the 1990 American romantic comedy film Pretty Woman (Credit: Buena Vista Pictures Distribution)

Keeping this in mind, here are five straightforward tips to help you confidently style those boots with class.

We’re presenting these tips not for the seasoned stylists but for those who are completely clueless and feeling fashion-confused.

1. Keep Away From High Shine

This is a very simple rule to follow. Stick to suede boots. You can go with classic leather, but avoid the ones that are glazed or buffed to shine.

Emily Ratajkowski has shown us time and time again that it's possible to wear over-the-knee boots without looking trashyEmily Ratajkowski has shown us time and time again that it’s possible to wear over-the-knee boots without looking trashy (Credit: WENN)

Of course, forget patent leather as well. As we said earlier, thigh-high boots are already a major fashion statement, so you don’t really need to add high-shine drama to get noticed.

Emily Ratajkowski wears a Zimmermann Emily Ratajkowski wears a Zimmermann “Esplanade” crepe body dress and Brian Atwood “Odille” suede thigh-high boots (Credit: WENN)

Besides, the goal is to avoid looking like “Pretty Woman.”

2. Strike a Balance

It’s no secret that short skirts (or dresses) look great with over-the-knee high boots — but only in moderation.

Showing a glimpse of your thighs is very alluring, but keep it to 3 inches max. If you want to push it, try maybe 5 inches.

Olivia Palermo is an expert at styling over-the-knee boots with a wide range of classy outfitsOlivia Palermo is an expert at styling over-the-knee boots with a wide range of classy outfits (Credit: WENN)

Once you do that, remember to cover up on top.

Wear a long-sleeved mini dress, or top your outfit with a chunky coat or sweater to tone down the sexiness.

Olivia Palermo caps off her structured outfit with gray suede over-the-knee bootsOlivia Palermo caps off her structured outfit with gray suede over-the-knee boots (Credit: WENN)

We love how Olivia Palermo stylishly finished her structured suit with gray over-the-knee boots at the Carven presentation during Paris Fashion Week.

3. Keep it Monochromatic

The easiest way to wear over-the-knee boots is by pairing them with skinny jeans or leggings.

But do yourself a favor by keeping the ensemble monochromatic. Not only will you look classier, but you will look taller, too.

A beautiful young blonde woman shows how to wear black over-the-knee boots in winterA beautiful young blonde woman shows how to wear black over-the-knee boots in winter (Credit: Andrey Arkusha / Shutterstock)

Try wearing black-on-black for that leg-lengthening effect.

If you want to be a little playful, try dark tones with some print or texture to give you a little contrast without making it too obvious.

4. Stay Away From Extreme Heels and Platforms

Platforms and sky-high stilettos are great, but when it comes to over-the-knee boots, you actually don’t need such extras.

While it is a matter of personal preference and opinion, it’s so much easier to rock extra tall boots when they’re not too high, not too pointy, and with heels that are not as needle-thin.

5. Try Other Colors

Don’t be afraid to try (thigh-high) boots in other colors. If you’re not that adventurous, go with camel, tan, brown, or gray neutrals.

If you want more drama, red and purple boots aren’t that hard to find, either.

On September 11, 2015, during New York Fashion Week, Kim Kardashian showcased her style prowess while heading out for dinner with a friend in Soho, effortlessly pairing a long black coat, black knee-high boots, and a Metallica t-shirtOn September 11, 2015, during New York Fashion Week, Kim Kardashian showcased her style prowess while heading out for dinner with a friend in Soho, effortlessly pairing a long black coat, black knee-high boots, and a Metallica t-shirt (Credit: WENN)

That said, always remember to go for monochromatic to avoid looking like your legs were cut in half.

In the case of brighter boots, let them be the focal point or highlight of your outfit by wearing them with classic or neutral separates.

So, are you ready to sport some over-the-knee boots this season?

Filed Under: Shoe Styles