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Stars Slaying In Mini Skirts & Thigh-High Boots: Photos Of Hailey Baldwin & More

By:
Jennifer Phang
September 21, 2022 12:30PM EDT

Mini skirts paired with thigh-high boots are the perfect combination. See stars like Hailey Baldwin with the best inspiration for this sexy look!

1 of 19

Stars In Skirts & Thigh-High Boots

Stars In Skirts & Thigh-High Boots
AP Images

As the weather chills, we’re all looking for cold weather looks. And we already know we’ll be rocking more than pants this season, thanks to thigh-high boots! High boots provide coverage while also showing some leg, perfect for a sassy fall or winter look. Over the years, celebrities have favored pairing their short skirts with various versions of the thigh-high boot, and stars like Paris Hilton, Bella Thorne, Olivia Culpo and more have totally mastered the trend.

Of course, the style isn’t just for the coldedr months, as Olivia and Paris proved by pairing their skirts and boots with a tank top and crop top, respectively. Meanwhile, Bella added some mesh tights to hers for a cooler-weather vibe. Others stars who have taken on this style over the years include Miley Cyrus, Taylor Swift and many more.

Keep scrolling through the gallery to check out celebrities wearing skirts and pairing them with thigh-high boots!

January 27, 2021, 4:08PM
2 of 19

Rihanna Heading To Dinner In NYC

Rihanna Heading To Dinner In NYC
WavyPeter / SplashNews.com

Rihanna rocks a mini skirt with boots while out and about in New York City on May 4, 2023. She was pregnant with her second child at the time.

May 5, 2023, 7:42AM
3 of 19

Dakota Johnson

Dakota Johnson
Moda Milano/IPA / SplashNews.com

Dakota Johnson at the GUCCI Fashion Show during Milan Fashion Week. She wore a black lace outfit that included a mini skirt and blazer. 

February 24, 2023, 5:34PM
4 of 19

Kendall Jenner

Kendall Jenner
Eric Kowalsky / MEGA

Kendall Jenner looked fab in a sheer shirt and white mini while leaving her New York City hotel with pal Fai Khadra on Sep. 19, 2022. She teamed the look with a little white Prada bag and knee-high boots.

September 20, 2022, 8:26AM
5 of 19

Billie Eilish

Billie Eilish
HEDO / BACKGRID

Billie Eilish stuns while arriving at Kaia Gerber’s 21st birthday hosted by Connor Treacy at Off Sunset in Hollywood. She rocked thigh high boots and a mini skirt to the event. 

September 4, 2022, 12:29PM

More AboutOlivia Culpo

  • Christian McCaffrey’s Wife: All About Olivia Culpo & Their Relationship
6 of 19

Julia Fox

Julia Fox
RACHPOOT.COM / SplashNews.com

Julia fox shows off her physique in another self-made outfit during outing in Los Angeles. Her boots crept up past her thighs.

March 25, 2022, 8:57AM
7 of 19

Hailey Baldwin

Hailey Baldwin
Shutterstock

Hailey Baldwin attends Paris Fashion Week in February 2020. She wore a green blazer and matching, high-waisted skirt along with thigh-high black boots.

December 22, 2021, 8:20AM
8 of 19

Miley Cyrus

Miley Cyrus
PALACE LEE / SplashNews.com

Miley Cyrus is all smiles while out and about in London. She wore a black leather skirt with a black turtleneck and leather boots.

December 22, 2021, 8:55AM
9 of 19

Chrissy Teigen

Chrissy Teigen
SplashNews.com

Chrissy Teigen hits the streets of New York City in an animal print skirt. She paired the look with a black long-sleeved shirt and black boots.

December 22, 2021, 8:56AM
10 of 19

Bella Thorne

Bella Thorne
Broadimage/Shutterstock

Bella Thorne walks The Celebrity Experience red carpet in Jan. 2019. She rocked a sheer black top and leather skirt, along with Fendi boots.

December 22, 2021, 8:55AM
11 of 19

Olivia Culpo

Olivia Culpo
TK/STAR MAX/IPx

Olivia Culpo makes an appearance at AOL Build Series in September in New York City. She geared up for fall by rocking bright blue thigh high boots, which matched her tank top. The look was complete with a high-waisted skirt.

January 27, 2021, 4:08PM
12 of 19

Charli XCX

Charli XCX
Donald Traill/Invision/AP

Charli XCX wears a velvet crop top and matching skirt with thigh-high slit, which she paired with black boots. The look was perfect for the BooHoo.com launch party in 2015.

January 27, 2021, 4:08PM
13 of 19

Kim Kardashian

Kim Kardashian
Mpi67/MediaPunch/MediaPunch/IPx

Kim Kardashian hits the streets of New York City in a mini skirt, long t-shirt, and black thigh-high boots. She also wore a fur coat over her shoulders amidst her second pregnancy.

 

January 27, 2021, 4:08PM
14 of 19

Hailey Baldwin

Hailey Baldwin
Abaca / FameFlynet / SplashNews.

Hailey Baldin looks super chic and stylish while attending Paris Fashion Week. She wore a grey skirt with black, thigh-high boots and a black shirt. Her look was also complete with a long green coat.

January 27, 2021, 4:08PM
15 of 19

Bella Thorne

Bella Thorne
Star Max/IPx

Bella Thorne looks fierce in a pink skirt and lace-up black boots, which she paired with a t-shirt and mesh tights. She also wore a hat and stuck her tongue out for a fully rocker look.

January 27, 2021, 4:08PM
16 of 19

Draya Michele

Draya Michele
zz/OGUT/STAR MAX/IPx

Draya Michele steps out for a night out in Hollywood in Jan. 2020. She wore a crop top and skirt set, which she paired with heeled white boots.

January 27, 2021, 4:08PM
17 of 19

Hilary Duff

Hilary Duff
MEGA

Hilary Duff is photographed heading to lunch in Los Angeles in a denim skirt and white sweater. She also rocked thigh-high boots and a scarf to keep warm.

 

January 27, 2021, 4:08PM
18 of 19

Paris Hilton

Paris Hilton
KGC-305/STAR MAX/IPx

Paris Hilton poses for photos during an appearance in London, England. She wore a crop top and skirt, which she paired with a heart-shaped bag and black boots.

January 27, 2021, 4:08PM
19 of 19

Larsa Pippen

Larsa Pippen
zz/GOTPAP/STAR MAX/IPx

Larsa Pippen slays in a high-wasted leather skirt and sheer top while out in Hollywood. She also rocked thigh-high black boots with the outfit.

January 27, 2021, 4:08PM
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