Though it may seem like Olivia Rodrigo became an overnight sensation with the release of her debut single, “Drivers License,” in 2021, the then-17-year-old was already an industry veteran. Enrolling in acting and voice lessons at an early age, Rodrigo’s initial break came courtesy of Disney, when she was cast in the television series Bizaardvark at the age of 12. A starring role in High School Musical: The Musical: The Series, a musical drama inspired by Disney’s High School Musical franchise, immediately followed, with Rodrigo landing a record deal by 2020. That’s when the California native’s meteoric rise as a singer and songwriter took off, and it’s shown no signs of slowing down since.

As award nominations quickly piled up for her debut album, Sour, Rodrigo began honing a red carpet style befitting her pop star status—but always with a punk-rock twist. Her street style looks have followed a similar (albeit more casual) theme, with the singer often captured by paparazzi in miniskirts (sometimes pleated, sometimes plaid), graphic tees and Doc Martens. “I try to shop vintage, mostly,” Rodrigo told British Vogue. “I love a Depop or The Real Real purchase,” she said of her everyday clothes, adding, “I look for quality, and I like pieces that are kind of funky and weird.” That penchant for vintage pieces in her personal wardrobe has also occasionally found its way into Rodrigo’s workwear, with the “Vampire” singer donning vintage designs like a Betsey Johnson slip dress for her Sour Prom concert premiere and a tweed Chanel set from the ‘90s during a visit to the White House.

From her earliest red carpet days in jeans and sneakers to rocking custom couture creations while accepting a Grammy Award, take a look at Rodrigo’s style journey so far.

Subscribe to Observer’s Lifestyle Newsletter

Following the Disney debut of Bizaardvark, Rodrigo attended a benefit event hosted by Mattel in a casual ripped jeans and sneakers look. Though her sartorial taste would change drastically within the next five years, Rodrigo had already established her signature long, glossy hairstyle.

Experimenting with patterns and colors, Rodrigo paired a ruffled miniskirt with red and green stripes with a blousy polka-dotted top to a movie premiere in 2017.

Closer to her current style, Rodrigo wore an icy blue dress with metallic embroidery to the premiere of the fifth installment of the Pirates of the Caribbean series. The singer paired the midi dress with matching metallic sandals and a barely-there beauty look that included cascading curls.

Rodrigo opted for a more classic ensemble at the Chinese American Film Festival, choosing a black fringe dress with sheer sleeves, which she paired with a bold lip.

The High School Musical: The Musical: The Series premiere marked Rodrigo’s first major red carpet event where all eyes were on her. Instead of a dress, the singer went a slightly unexpected route in a black tulle skirt. The floor-length silhouette included a touch of sparkle with floral embroidery along the waist, and Rodrigo paired the........

© Observer