How to Wear Over-the-Knee Boots Without Looking Like “Pretty Woman”

Please subscribe to our newsletter to receive updates from Your Next Shoes. This post may contain affiliate links. Please see our disclosure for more details.

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 end up looking nasty or, worse, like “Pretty Woman”!

Yes, we’ve all seen “Pretty Woman”. And the image of Julia Roberts in her micro-mini skirt and super-shiny over-the-knee boots is probably what’s keeping the majority of the women on this planet from trying on that extra “tall order.” But here’s the thing, 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. With this in mind, here are 5 simple tips to follow so you can rock those boots with class. We’re laying these out not for the seasoned stylistas, but for the completely clueless and (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. Of course, forget patent leather as well. Like 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. Besides, the goal is to veer away from looking like “Pretty Woman”, right?

Emily Ratajkowski at BBC Radio on August 11, 2015, in London, England, to promote her new movie 'We Are Your Friends'Emily Ratajkowski at BBC Radio on August 11, 2015, in London, England, to promote her new movie ‘We Are Your Friends’

Emily Ratajkowski wears a Zimmermann "Esplanade" crepe body dress and Brian Atwood "Odille" suede thigh-high bootsEmily Ratajkowski wears a Zimmermann “Esplanade” crepe body dress and Brian Atwood “Odille” suede thigh-high boots

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.

Once you do that, remember to cover up on top. Go for a long-sleeved mini dress, or top your outfit with a chunky coat or sweater to tone down the sexiness. A good example is how Ruxandra Ioana of ‘From Brussels’ with Love styled her super tall boots.

Ruxandra keeping it sexy yet prim by topping her skirt and boots with a tailored jacketRuxandra keeping it sexy yet prim by topping her skirt and boots with a tailored jacket

And, of course, who can forget the way Olivia Palermo stylishly finished her structured suit with gray over-the-knee boots at the Carven presentation during Paris Fashion Week.

Olivia Palermo attends the Carven show during Paris Fashion Week in France on September 26, 2013Olivia Palermo attends the Carven show during Paris Fashion Week in France on September 26, 2013

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

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. Like Nika of Fashion Agony, go 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 just a little bit of contrast without making it too obvious.

Nika Huk elongates her legs by pairing her black thigh-high leather boots with black leggings Nika Huk elongates her legs by pairing her black thigh-high leather boots with black leggings 

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 neutrals, such as camel, tan, brown, or gray. If you want more drama, red and purple boots aren’t that hard to find as well.

That said, always remember to go for monochromatic to avoid looking like your legs were cut in half. In case of brighter boots, let them be the focal point or highlight of your outfit by wearing them with classic or neutral separates.

Kim Kardashian rocking a long black coat, black knee-high boots, and a Metallica t-shirtKim Kardashian rocking a long black coat, black knee-high boots, and a Metallica t-shirt, heads out for dinner with a friend in Soho during New York Fashion Week on September 11, 2015

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

Credit: WENN

Kardashian-Jenner Siblings Wear Archival Dolce & Gabbana to Kravis Wedding Festivities

The Kardashian-Jenner family has taken Italy by Storm with their archival Dolce & Gabbana looks for Kourtney Kardashian and Travis…

Heidi Klum Kisses Husband Tom Kaulitz in Strapless Nightshift Dress

Heidi Klum was invited to be one of the presenters at the 2022 Billboard Music Awards, and she certainly didn’t…

Heidi Klum Stuns in Dolce & Gabbana Green Sequined Menswear Suit While Sofia Vergara Wows in O’Blanc Beaded Feather Dress

Heidi Klum and Sofia Vergara had quite a fashion showdown at America’s Got Talent season 17 kick-off event held at…

AGT’s Heidi Klum Stars in Kim Kardashian’s Sultry SKIMS Campaign Ad

She recently joined her fellow supermodels, including Tyra Banks, Alessandra Ambrosio, and Candice Swanepoel, in a sultry photoshoot for Kim…

Sandra Bullock Flaunts Cleavage in Pink Ombre Tulle Gown and Thigh-High Boots at The Lost City Premiere

She sure knows how to make an entrance! Sandra Bullock made a stunning appearance at the Los Angeles premiere of…

Khloe Kardashian Sparks Romance Rumors With Ex Trey Songz in Mugler See-Through Dress and Amina Muaddi Boots

The 37-year-old reality TV star has been hitting the gym hard and proudly showing off her revenge body amid her…

Jennifer Lopez Reveals Extreme Toe Cleavage in Hardot’s Harlot Pumps

She had been busy on the promo circuit for her latest movie, Marry Me, which was theatrically released on February…

Miley Cyrus Visits Pete Davidson’s Apartment After Serenading Him With It Should Have Been Me Cover

Miley Cyrus and Pete Davidson are ringing in the new year together! The two are set to host NBC’s year-end…

Ben Affleck Was Jennifer Lopez’s the One That Got Away, Ex Manager Predicts Imminent Wedding

Things are heating up between Ben Affleck and Jennifer Lopez since rekindling their romance in the spring of 2021. And…

Paris and Nicky Hilton Kick off Holiday Season With Chla’s Toy Drive in Alice + Olivia and Alessandra Rich Christmas Plaid Outfits

The Hiltons kicked off the holiday season early! Socialites Paris and Nicky and their mom Kathy co-hosted the 16th annual…

Irina Shayk Channels Clueless’ Cher Horowitz in Vivienne Westwood Plaid Skirt Suit and Magda Butrym Knee-High Combat Boots

She has been stepping up her fashion game over the past year amid the pandemic. And recently, Irina Shayk seems…

6 Best Riding Boot Brands and Most Popular Equestrian Boots

So, you’re intrigued by riding boots, and you can picture yourself wearing a pair. Your next question is probably, where…

Olivia Palermo Walks Over Snow Pile in Gianvito Rossi Marsden Over-the-Knee Boots

She has been keeping her winter fashion game strong. And last week, Olivia Palermo pulled out all the stops as…

Celine Dion Postpones Two Courage World Tour Dates; Tests Negative for COVID-19

One day after finishing a six-show run around New York City, Celine Dion and her team announced that the singer…

Heidi Klum’s Veiny Feet Look Ready To Burst: Kicks Off Her America’s Got Talent Return

She served as a judge on America’s Got Talent for six seasons, from 2013 to 2018, as well as on…

Hailey Bieber Styles Saks Potts Leather Outfit With Pink Heels in Paris

She may be taking a break from walking the catwalk, but Hailey Bieber is making sure she doesn’t miss out…

Nicole Scherzinger’s Friends Beg Her to Stop Dating X Factor Celebrity’s Thom Evans

Nicole Scherzinger is rumored to be dating rugby player turned popstar Thom Evans after weeks of exchanging flirty text messages….

A-List Celebrities Support Their Favorite Designers at 4th Annual WWD Honors

Women’s Wear Daily hosted its fourth annual WWD Honors at the InterContinental New York Barclay in New York City two…

What Is Ali Larter’s Net Worth? Resident Evil Star in Sexy Thigh-High Boots

Best known for playing the dual roles of Niki Sanders and Tracy Strauss on the NBC science fiction drama Heroes,…

Reptile Embossed Over-the-Knee Winnie Harlow x Steve Madden Boots

Discovered by America’s Next Top Model host Tyra Banks on Instagram, Winnie Harlow made her debut on season 21 of…

© Copyright Your Next Shoes 2010 - 2022 | Back to Top