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.
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![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](https://footwearnews.com/wp-content/uploads/2021/10/spl1680229_037.jpg?w=731)
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.
![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](https://footwearnews.com/wp-content/uploads/2021/10/SPL5238968_002.jpg?w=1024)
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](https://footwearnews.com/wp-content/uploads/2021/10/SPL5257884_009.jpg?w=683)
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.](https://footwearnews.com/wp-content/uploads/2021/10/MEGA786498_001.jpg?w=688)
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](https://footwearnews.com/wp-content/uploads/2021/10/SPL5256215_046.jpg?w=532)
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.
![Academy Museum of Motion Pictures Opening Gala](https://footwearnews.com/wp-content/uploads/2021/10/SPL5260596_015.jpg?w=705)
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.
Click through the gallery to see more of Olivia Rodrigo’s red carpet style evolution.