See Olivia Rodrigo's Hardcore '90s Style in 15 Outfits

Published on 11/7/2023 at 4:04 PM

While many young celebrities have adopted '90s and early-2000s fashion trends, there's one star who's mastered it every time: Olivia Rodrigo. Although she's only 20, the pop singer has quickly become a budding style maven to watch, from being a Disney Channel star to becoming one of Gen Z's most beloved artists. While her journey is still evolving, Rodrigo has produced many fashion moments for us to enjoy, from her captivating performances to her August 2023 Vogue cover.

Since first capturing the world's attention with her breakthrough single, "Drivers License," Rodrigo has gravitated toward silhouettes that are relatively simple yet statement-making, especially on the red carpet. Just days ago, she attended the 38th annual Rock & Roll Hall of Fame Induction Ceremony in a Valentino LBD with a rosette at the neckline and chunky heels to match, in line with her usual aesthetic. She rocks minidresses and boots with almost every appearance, and her red sweetheart Magda Butrym design, sequined chest-cutout Grammys afterparty dress, and purple Versace corset at the iHeartRadio Music Awards are prime examples. She also dabbles with gowns, such as her '90s-inspired slip dress for the Canadian Songwriters Hall of Fame Gala and her black-and-white Thom Browne floral sheath at the 2023 Met Gala.

The "Sour" musician's street style is just as noteworthy, where her penchant for vintage shopping is made even more obvious. Most notably, Rodrigo visited the White House in a vintage Chanel pink tweed suit and six-inch platforms, effortlessly nodding to the archival trend from the Parisian fashion house. She's also showcased a host of edgier looks, including the cropped sweater, camo miniskirt, and infamous Marc Jacobs platform boots she wore for an art exhibit and the Hellcat baby tee and Miu Miu loafers she sported while out in New York City in September.

Ahead, take a moment to appreciate Rodrigo's lineup of memorable style moments thus far.

Olivia Rodrigo at the November 2023 Rock & Roll Hall of Fame Ceremony

For the 38th Rock & Roll Hall of Fame ceremony, Rodrigo stayed true to her love for minidresses with a black Valentino LBD and chunky platform sandals to match.

Olivia Rodrigo at the 2023 MTV VMAs

The young star stunned on the 2023 MTV VMAs carpet in a custom silver Ludovic de Saint Sernin gown made with 150,000 Swarovski crystals.

Olivia Rodrigo in New York City in September 2023

While en route to the SiriusXM Studios in New York City, Rodrigo wore a Hellcat T-shirt, a white tennis skirt, Miu Miu loafers, and Prada sunglasses.

Olivia Rodrigo in London in August 2023

The "Good 4 U" artist wore a red sweetheart minidress from Magda Butrym while out in London. She accessorized with coordinating kitten heels and silver jewelry.

Olivia Rodrigo at the 2023 Met Gala

For the 2023 Met Gala, Rodrigo tapped into Old Hollywood glamour in a custom black-and-white dress by Thom Browne, made from strings and flowers.

Olivia Rodrigo at the November 2022 Rock & Roll Hall of Fame Induction Ceremony

Rodrigo performed at the 37th annual Rock & Roll Hall of Fame Induction Ceremony in a pleated miniskirt and a cutout corset top by Shushu Tong.

Olivia Rodrigo at the Spring 2023 Givenchy Runway Show

Rodrigo attended Givenchy's spring/summer 2023 show during Paris Fashion Week in a full cream ensemble by the brand that featured a plunging slip dress, a coat, and chunky heels.

Olivia Rodrigo at the 2022 MTV Movie & TV Awards

The "Vampire" singer turned into the ultimate Y2K queen in a vintage black corset dress by Jean Paul Gaultier and heeled sandals to match for the 2022 MTV Movie & TV Awards. She accessorized with silver jewelry and a slicked-back bun with hair sticking out on both sides.

Olivia Rodrigo at the 2022 Met Gala

For the 2022 Met Gala, Rodrigo remained true to her 2000s-inspired fashion sense with a purple sparkly Versace gown, matching platform heels, and butterfly clips in her hair.

Olivia Rodrigo at the 2022 Grammy Awards

For her first Grammys, the pop-rock star wore a custom off-the-shoulder Vivienne Westwood gown that included a bedazzled pink outline and opera gloves.

Olivia Rodrigo at the 2022 BRIT Awards

For the BRIT Awards, Rodrigo wowed in a silver metallic dress by Alexandre Vauthier Couture with black heels.

Olivia Rodrigo at a January 2022 Art Exhibit

Rodrigo wore a cropped sweater, a camouflage miniskirt, and the infamous Marc Jacobs Kiki boots while visiting the "Artists Inspired by Music: Interscope Reimagined" art exhibit in Los Angeles.

Olivia Rodrigo at the 2021 Variety Hitmakers Brunch

Rodrigo celebrated her songwriter of the year win at Variety's Hitmakers Brunch in a Calvin Luo minidress with a green bow across the front. She layered the dress over a black mesh top and accessorized with knee-high socks and velvet Mary Jane platforms.

Olivia Rodrigo at the 2021 Met Gala

For her first Met Gala, Rodrigo rocked a black feather and lace sheer Saint Laurent catsuit with matching chunky heels and diamond waterfall earrings.

Olivia Rodrigo at the White House in July 2021

During a visit to the White House, Rodrigo rocked a vintage Chanel pink tweed skirt suit with black socks and white Giuseppe Zanotti heels. She topped the look with a Chanel chain belt and a mini handbag.