Olivia Rodrigo Style Transformation Over the Years

Olivia Rodrigo is a huge fan of the early 2000s fashion and loves to be styled in the latest Y2K trends. It makes sense that the singer would dabble in what is now retro-inspired style since she was born in 2003 and missed embracing the iconic looks of the era.

The “Jealousy, Jealousy” artist has been at the top of the music charts with her breakout hit album “Sour” and also sits at the top of the fashion world’s radar, too. Rodrigo is often spotted in colorful garments, mixed prints and lots of jewelry. It appears that her favorite choice of footwear includes platform boots and chunky heels, with styles that are from a mix of luxury and affordable brands like Doc Martens, Marc Jacobs and Naked Wolfe.

Here, take a look at the former Disney “Bizaardvark” star’s standout style evolution.

November 8, 2017 Hollywood, CA Vanessa Lyon 'Coco' U.S. Premiere held at the El Capitan Theatre © Janet Gough / AFF-USA.com. 08 Nov 2017 Pictured: Olivia Rodrigo. Photo credit: MEGA TheMegaAgency.com +1 888 505 6342 (Mega Agency TagID: MEGA113704_042.jpg) [Photo via Mega Agency] — Olivia Rodrigo at Disney Pixar’s ‘Coco’ movie premiere November 8, 2017 in Hollywood, Calif.

CREDIT: MEGA

When Rodrigo attended Disney Pixar’s “Coco” movie premiere on Nov. 8, 2017 in an ankle-length red dress and perfectly matched heels, she looked effortlessly chic. The outfit included ruffles with the bottom hem meeting the ballet-style heels adorned with ankle ribbons.

The 2018 Radio Disney Music Awards at The Loews Hollywood Hotel in Hollywood, California on 6/22/18. 22 Jun 2018 Pictured: Olivia Rodrigo. Photo credit: River / MEGA TheMegaAgency.com +1 888 505 6342 (Mega Agency TagID: MEGA244227_002.jpg) [Photo via Mega Agency] — The 2018 Radio Disney Music Awards at The Loews Hollywood Hotel in Hollywood, Calif., on June 6.

CREDIT: River / MEGA

Still with Disney in 2018, Rodrigo embraced a more playful style in a black iridescent sequined top and coral trousers at the Radio Disney Music Awards on June 6. The songstress completed the look in strappy brown platform sandals.

Celebrities arrive at the .My Friend's Place' 30th Anniversary Gala.Pictured: Olivia Rodrigo,Chad L. ColemanConstance ZimmerRuss LamoureuxEli GoreeElliot KnightGiacomo GianniottiGuestHannah ZeileJack BlackJonathan FernandezLukas GrahamMaddie ZieglerMadison HuMark JacksonOlivia RodrigoRayvon OwenShane Bitney CroneSirahSummer ChastantRef: SPL1680229 070418 NON-EXCLUSIVEPicture by: SplashNews.comSplash News and PicturesUSA: +1 310-525-5808London: +44 (0)20 8126 1009Berlin: +49 175 3764 166photodesk@splashnews.comWorld Rights, No Austria Rights, No Germany Rights, No Switzerland Rights — Olivia Rodrigo at the “My Friend’s Place” 30th Anniversary Gala in 2018.

CREDIT: SplashNews.com

For the 2018 “My Friend’s Place” 30th Anniversary Gala, her black mini dress incorporated a red velvet flower motif to match the event’s backdrop on April 6. She anchored the outfit with red pumps that featured ribbons around the ankle.

Maleficent: Mistress of Evil - World Premiere - Arrivals. 30 Sep 2019 Pictured: Olivia Rodrigo. Photo credit: MEGA TheMegaAgency.com +1 888 505 6342 (Mega Agency TagID: MEGA517447_043.jpg) [Photo via Mega Agency] — “Maleficent: Mistress of Evil” world premiere on Sept. 30, 2019.

CREDIT: MEGA

Rodrigo shined at the world premiere for Disney’s “Maleficent: Mistress of Evil” in a metallic gold pant set. Her black sandal heels featured a tinted PVC strap across the top of her foot.

Olivia Rodrigo, arrives during a news conference in the James S. Brady Press Briefing Room with Jen Psaki, White House press secretary, at the White House in Washington, D.C., U.S., on Wednesday, July 14, 2021. Credit: Oliver Contreras / Pool via CNPPictured: Olivia Rodrigo,Jen PsakiRef: SPL5238968 140721 NON-EXCLUSIVEPicture by: Oliver Contreras / Pool via CNP / SplashNews.comSplash News and PicturesUSA: +1 310-525-5808London: +44 (0)20 8126 1009Berlin: +49 175 3764 166photodesk@splashnews.comWorld Rights, No France Rights — Olivia Rodrigo at the White House daily press briefing on July 14, 2021.

CREDIT: Oliver Contreras / Pool via CNP / SplashNews.com

Rodrigo wore a vintage Chanel pink tweed skirt set to met with President Joe Biden for a vaccination press release on July 14. The Chanel outfit resembled a schoolgirl uniform when paired with her high black socks and white platform heels from Giuseppe Zanotti.

September 18, 2021, Las Vegas, Nevada: Olivia Rodrigo performs at iHeartRadio Daytime Village — Olivia Rodrigo performs at iHeartRadio in Las Vegas on Sept. 18, 2021.

CREDIT: Zuma / SplashNews.com

The “Driver’s License” singer performed her first major show on Sept. 18 at the iHeartRadio Music Festival in Las Vegas. Rodrigo entertained the crowd with the 20-minute gig in a black long-sleeve crop top with asymmetric cutouts and blue high waisted tailored trousers. The outfit had some punk rock vibes with a chain grommet belt and the top’s sleeves coming over her hands like fingerless gloves.

MTV VMAs 2021. Olivia Rodrigo. — Olivia Rodrigo at the MTV VMAs 2021.

CREDIT: MEGA

Rodrigo wowed at the MTV Video Music Awards on Sept. 12 in a vintage 2001 Versace spring dress. The strapless gown had a floor-length hem that hid her shoes.

Celebrities arrive at the 2021 Met Gala celebrating American Fashion wearing Ralph Lauren. This year's theme, "In America: A Lexicon of Fashion," will honor the 75th anniversary of the museum's Costume Institute and "explore a modern vocabulary of American fashion," the museum said.Pictured: Olivia RodrigoRef: SPL5256215 130921 NON-EXCLUSIVEPicture by: Ron Adar/M10s / SplashNews.comSplash News and PicturesUSA: +1 310-525-5808London: +44 (0)20 8126 1009Berlin: +49 175 3764 166photodesk@splashnews.comWorld Rights — Olivia Rodrigo arrives at the 2021 Met Gala celebrating American Fashion.

CREDIT: Ron Adar/M10s / SplashNews.com

In the most daring outfit yet, Rodrigo walked the steps of the Met Gala on Sept. 13 in a see-through jumpsuit that featured velvet ostrich feathers with lace sleeves and pant legs. Rodrigo wore sky-high platforms for an extra dose of drama.

Rodrigo turned heads again when she attended the Academy Museum of Motion Pictures‘ opening gala on Sept. 26 in a Saint Laurent gown. The black sheath dress had a thigh-high split and a large geometric shape cut out of the bustier.

See Olivia Rodrigo, Addison Rae and more Gen-Z style stars.