Olivia Rodrigo’s Hottest Photos – Hollywood Life

Olivia Rodrigo’s Hottest Outfits: Photos of the Singer’s Sexiest Looks

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February 20, 2024 9:49AM EST
Olivia Rodrigo
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No more teen angst, Olivia Rodrigo is 21 years old now! Celebrate her birthday with photos of all her hottest looks.

Get ready to be dazzled by the one and only Olivia Rodrigo – not only is she a chart-topping singer, but she’s also a total fashion icon! From the moment she burst onto the scene, this former Disney star has been slaying with her girly, fun style, drawing inspiration from the best 90s trends. Think pink, plaids, crop tops, and chunky shoes – this girl knows how to keep it fresh and fun!

But don’t be fooled by her playful side, because Olivia can also bring the glamour like nobody else. Whenever she hits the red carpet, she turns heads with her sparkling gowns and sleek silhouettes. And let’s not forget about those chic accessories – whether it’s gloves or platform heels, she knows how to make a statement.

Ready for more of Olivia’s hottest looks? Check out our fashion expert’s top picks and get inspired to steal her style!

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Olivia Rodrigo at the 2023 Grammys

Olivia Rodrigo at the 2023 Grammys
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Olivia Rodrigo was a sheer wonder at the 2023 Grammys. Her slinky Miu Miu slipdress dress revealed hints of a bra and hot pants, while she went for a makeup-minimal look. Striking Tiffany & Co. jewelry finished the job.

February 20, 2023, 10:00AM
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Olivia Rodrigo at a 2023 Grammy After Party

Olivia Rodrigo at a 2023 Grammy After Party
Xavier Collin/Image Press Agency

That’s the key! Olivia Rodrigo put on a dazzling display in a black dequined minidress with a sexy midriff cutout during Universal Music Group’s 2023 Grammys after party on Feb. 5, 2023. She added peep-toe platforms and swept her silky brown hair over her shoulders.

February 20, 2023, 9:59AM
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Olivia Rodrigo on Halloween

Olivia Rodrigo on Halloween
The Hollywood jr / BACKGRID

Darling! Olivia Rodrigo was an adorably sexy as Betty Boop at Kendal Jenner’s star-packed Halloween party, hosted by the model’s 818 tequila in Hollywood. Her curled bob, little red dress, and matching garter were too cute.

October 30, 2022, 4:54PM
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Olivia Rodrigo in West Hollywood

Olivia Rodrigo in West Hollywood
affinitypicture / BACKGRID

Olivia Rodrigo stunned in a crop top and pleated mini-skirt on Oct. 24, 2022. The good 4 u singer channeled her inner Britney Spears in an outfit similar to the pop icon’s Baby One More Time music video of the late 1990s.

October 24, 2022, 8:38PM
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Olivia Rodrigo & Billy Joel

Olivia Rodrigo & Billy Joel
Myrna Suarez/Shutterstock

Olivia Rodrigo poses backstage with Billy Joel at Madison Square Garden on Aug. 24, 2022. She surprised the crowd to sing Uptown Girl and her song Deja Vu at his show. Olivia rocked a mini skirt and corset top for the performance.

August 25, 2022, 8:02AM
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Olivia Rodrigo Arriving at Her Hotel in NYC

Olivia Rodrigo Arriving at Her Hotel in NYC
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Olivia Rodrigo is seen arriving at a hotel in New York City. She rocked a black slip dress with loafers and socks.

August 20, 2022, 10:35AM
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Olivia Rodrigo at the ‘HSMTSTM’ premiere

Olivia Rodrigo at the ‘HSMTSTM’ premiere
Stewart Cook/Shutterstock

Olivia Rodrigo at the High School Musical: The Musical: The Series red carpet premiere for its third season. She rocked a mini dress. 

July 27, 2022, 11:18PM
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Olivia Rodrigo Headlines Glastonbury

Olivia Rodrigo Headlines Glastonbury
Shutterstock

Olivia Rodrigo headlines Day 4 of the Glastonbury Festival in the UK on Jun. 25, 2022. Embracing her Y2K-chic style, she wore a purple plaid crop top and patterned skirt with matching arm warmers, knee-high combat boots, and fishnet tights.

July 26, 2022, 5:18PM
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Olivia Rodrigo at the 2022 MTV Movie & TV Awards

Olivia Rodrigo at the 2022 MTV Movie & TV Awards
Christopher Polk/Shutterstock

Olivia Rodrigo set pulses racing in a black Jean Paul Gaultier dress with a crossing halter top during the 2022 MTV Movie & TV Awards. She completed the look with thin strappy sandals and spiky space buns.

June 6, 2022, 5:20PM
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Olivia Rodrigo at the 2022 Met Gala

Olivia Rodrigo at the 2022 Met Gala
Matt Baron/Shutterstock

Olivia Rodrigo looked magical in lavender Versace during the 2022 Met Gala on May 2. Her long, curly locks were pinked back with butterfly clips and she donned sheer gloves.

May 4, 2022, 2:12PM
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Olivia Rodrigo After the 2022 Met

Olivia Rodrigo After the 2022 Met
WavyPeter / SplashNews.com

Olivia Rodrigo looks so cute in pink and red houndstooth while leaving a Met Gala afterparty on May 2, 2022. Her braids and black platform heels were the perfect additions.

May 4, 2022, 2:12PM
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Olivia Rodrigo at the 2022 Grammys

Olivia Rodrigo at the 2022 Grammys
David Fisher/Shutterstock

Olivia Rodrigo wows in black Viviene Westwood with purple details as she takes the red carpet of the 64th Annual Grammy Awards on Apr. 3, 2022. Gloves and choker necklaces added some old school glamour to the look.

May 4, 2022, 2:12PM
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Olivia Rodrigo Performs at the 2022 Grammys

Olivia Rodrigo Performs at the 2022 Grammys
Rob Latour/Shutterstock

Olivia Rodrigo belts her heart out while donning Givenchy on stage during the 64th Annual Grammy Awards on Apr. 3, 2022. She gave the look her own twist with combat boots and fishnet tights.

May 4, 2022, 2:16PM
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Olivia Rodrigo at the ‘Driving Home 2 U Premiere’

Olivia Rodrigo at the ‘Driving Home 2 U Premiere’
MediaPunch/Shutterstock

Olivia Rodrigo was so cute at the premiere of her Disney+ special Olivia Rodrigo: Driving Home 2 U in LA on Mar. 24, 2022. Bows made the look extra sweet.

May 4, 2022, 2:16PM
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Olivia Rodrigo at the 2022 iHeartRadio Music Awards

Olivia Rodrigo at the 2022 iHeartRadio Music Awards
Scott Kirkland/PictureGroup for/

Olivia Rodrigo keeps it classy in a purple dress and leather leggings during her appearance at the 2022 iHeartRadio Music Awards in LA. She teamed the Versace outfit with a high ponytail.

May 4, 2022, 2:16PM
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Olivia Rodrigo at the 2022 BRIT Awards

Olivia Rodrigo at the 2022 BRIT Awards
Matt Baron/Shutterstock

Olivia Rodrigo sparkles at the 42nd BRIT Awards in London on Feb. 8, 2022. Her mirrored dress was exquitist.

February 24, 2022, 8:51PM
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Olivia Rodrigo Wins at the 2022 BRIT Awards

Olivia Rodrigo Wins at the 2022 BRIT Awards
Anthony Harvey/Shutterstock

Olivia Rodrigo wins International Song of the Year at the BRITS. She held her trophy up proudly.

February 24, 2022, 8:51PM
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Olivia Rodrigo at Variety’s 2021 Music Hitmakers Brunch

Olivia Rodrigo at Variety’s 2021 Music Hitmakers Brunch
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Olivia Rodrigo was darling in a black Calvin Luo number with a big green bow as she arrived at the Variety 2021 Music Hitmakers Brunch presented by Peacock and Girls5eva and sponsored by IHG Hotels and Resorts held at the City Market Social House on December 4, 2021 in Los Angeles. Chunky shoes and tall socks completed the ensemble.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the AMAs

Olivia Rodrigo at the AMAs
Chris Pizzello/Invision/AP/Shutt

Olivia Rodrigo performed ‘Traitor’ at the American Music Awards on at Microsoft Theater in Los Angeles. She looked radiant while playing guitar in her white ensemble.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the 2021 American Music Awards

Olivia Rodrigo at the 2021 American Music Awards
Rob Latour/Shutterstock

Olivia Rodrigo stuns in a sparkling violet David Koma dress during the 2021 American Music Awards on Nov. 21. Sequins and feathers really made the look pop.

February 24, 2022, 8:51PM
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Olivia Rodrigo Performs at the 2021 MTV Video Music Awards

Olivia Rodrigo Performs at the 2021 MTV Video Music Awards
Charles Sykes/Invision/AP/Shutte

Olivia Rodrigo performs Good 4 U at the MTV Video Music Awards, in New York. Her princess-like dress was perfect for the performance of the pop punk hit.

February 24, 2022, 8:51PM
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Olivia Rodrigo Arrives for ‘Jimmy Kimmel Live’

Olivia Rodrigo Arrives for ‘Jimmy Kimmel Live’
Broadimage/Shutterstock

Olivia Rodrigo looked cool in a chartreuse skirt as she arrived for a taping of Jimmy Kimmel Live on Oct. 26, 2021. Her hair was in cute braids, tied with lime green bows that matched her look.

February 24, 2022, 8:51PM
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Olivia Rodrigo in 2021

Olivia Rodrigo in 2021
Amy Harris/Invision/AP/Shutterst

Olivia Rodrigo brings down the house during a taping of the Austin City Limits show on Oct. 2, 2021. Baggy pleather pants and a red top looked great together.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the Academy Museum of Motion Pictures Opening Gala

Olivia Rodrigo at the Academy Museum of Motion Pictures Opening Gala
Rob Latour/Shutterstock

Olivia Rodrigo stuns in a plunging black design during the opening of the Academy Museum of Motion Pictures on Sep. 25, 2021. Her hair was up in a sleek style and she added color with a red lip.

February 24, 2022, 8:51PM
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Olivia Rodrigo Plays iHeartRadio Music Festival

Olivia Rodrigo Plays iHeartRadio Music Festival
Matt Baron/Shutterstock

Olivia Rodrigo looks cute while playing iHeartRadio Music Festival in Las Vegas on Sep. 18, 2021. Her hair was in cute pigtails.

February 24, 2022, 8:51PM
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Olivia Rodrigo’s White House Visit

Olivia Rodrigo’s White House Visit
White House/News Pictures/Shutte

Vice President Kamala Harris meets with singer Olivia Rodrigo and her mother, Sophia Rodrigo at the White House in Washington DC on July 14, 2021. She was there to help promote COVID vaccinations to young people.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the 2021 Met Gala

Olivia Rodrigo at the 2021 Met Gala
Stephen Lovekin/Shutterstock

Olivia Rodrigo stuns in a Saint Laurent catsuit during the 2021 Met Gala in Sep of that year. Her sheer and feathered bodysuit went well with her sleek updo and smoky eyes.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the 2021 MTV Video Music Awards

Olivia Rodrigo at the 2021 MTV Video Music Awards
Jeremy Smith/imageSPACE/Shutters

Olivia Rodrigo looks glorious in Versace at the 2021 MTV Video Music Awards. The charmer flashed a peace sign at the crowd

February 24, 2022, 8:51PM
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Olivia Rodrigo at the 2021 BRIT Awards

Olivia Rodrigo at the 2021 BRIT Awards
Richard Young/Shutterstock

Olivia Rodrigo wows in red Dior during the 41st BRIT Awards on May 11, 2021. Stunning.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the 2021 BRIT Awards

Olivia Rodrigo at the 2021 BRIT Awards
Richard Young/Shutterstock

Neon dream! Olivia Rodrigo wows in yellow Dior during the 41st BRIT Awards on May 11, 2021.

February 24, 2022, 8:51PM
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‘High School Musical: The Musical – The Series’

‘High School Musical: The Musical – The Series’
Walt Disney Pictures/Kobal/Shutt

Olivia Rodrigo as Nini in High School Musical: The Musical – The Series. The very meta series was about students from the school where the High School Musical films were shot who staged a musical production based on the franchise.

February 24, 2022, 8:51PM
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Olivia Rodrigo in 2019

Olivia Rodrigo in 2019
Mark Von Holden/Invision/AP/Shut

Olivia Rodrigo poses at the Disney + launch event promoting High School Musical: The Musical: The Series on Oct. 19, 2019. Her yellow suit was peppered with white flowers.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the Premiere of ‘Maleficent: Mistress of Evil’

Olivia Rodrigo at the Premiere of ‘Maleficent: Mistress of Evil’
Richard Shotwell/Invision/AP/Shu

Go for the gold! Olivia Rodrigo glows at the premiere of the movie Maleficent: Mistress of Evil on Sep. 30, 2019.

February 24, 2022, 8:51PM
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Olivia Rodrigo at 2019 D23 Expo

Olivia Rodrigo at 2019 D23 Expo
Richard Shotwell/Invision/AP/Shu

Olivia Rodrigo attends the Disney+ press line at the 2019 D23 Expo, in Anaheim, California on Aug. 23. She was chic in a white turtleneck, red trousers, and silver platform heels.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the 2018 Radio Disney Music Awards

Olivia Rodrigo at the 2018 Radio Disney Music Awards
Matt Baron/Shutterstock

Olivia Rodrigo looks darling in pink pants and chunky black sequins during the Radio Disney Music Awards on Jun. 22, 2018. Her hair was in a high ponytail and she had on pink lipstick.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the Premiere of ‘Incredibles 2’

Olivia Rodrigo at the Premiere of ‘Incredibles 2’
Rob Latour/Shutterstock

Olivia Rodrigo is so chic in green silk pants and a polka dot top during the premiere of Incredibles 2 on Jun. 5, 2018. A star in the making.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the Premiere of ‘Thor: Ragnarok’

Olivia Rodrigo at the Premiere of ‘Thor: Ragnarok’
Rob Latour/Shutterstock

Olivia Rodrigo strikes a pose at the premiere of Thor: Ragnarok on Oct. 10, 2017. Her black lace dress was to-die-for.

February 24, 2022, 8:51PM
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Olivia Rodrigo at the Premiere of ‘Pirates of the Caribbean: Dead Men Tell No Tales’

Olivia Rodrigo at the Premiere of ‘Pirates of the Caribbean: Dead Men Tell No Tales’
Broadimage/Shutterstock

Olivia Rodrigo looks radiant at the premiere of Pirates of the Caribbean: Dead Men Tell No Tales on May 18, 2017. It was long before the success of Sour.

February 24, 2022, 8:51PM
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