The release of Olivia Rodrigo’s first single, “Drivers License,” in 2021 may have given the impression that she became an overnight sensation; nevertheless, although she was just 17 years old at the time, she was already an experienced talent in the field. After beginning her training in acting and voice acting at a young age, Rodrigo’s first big break came from Disney, when she was cast in the television series Bizaardvark when she was only 12 years old.
Almost soon after that, Olivia Rodrigo was offered a lead role in High School Musical: The Musical: The Series, a musical drama that was based on Disney’s High School Musical franchise. By the year 2020, he had also secured a record deal. The rapid rise of the California native as a singer and composer began at that point, and it has not shown any signs of slowing down since then. Olivia Rodrigo began crafting a red carpet style that matched her pop star status for her debut album, Sour, which swiftly accumulated a number of award nominations.
However, she always incorporated a punk-rock twist into her style. Paparazzi have frequently captured images of the singer wearing graphic tees, Doc Martens, and miniskirts (sometimes pleated, sometimes plaid). Her street-style outfits have followed a similar trend, albeit one that is more relaxed.
In an interview with British Vogue, Olivia Rodrigo stated, “I really try to shop vintage.” “I look for quality, and I like pieces that are kind of funky and weird,” she said about her everyday outfits. “I love a Depop or The Real Real purchase,” she added. “There is something about them that I find really cool.”
The “Vampire” singer has been known to wear vintage designs in her professional life, such as a Betsey Johnson slip dress for her Sour Prom concert premiere and a tweed Chanel set from the 1990s during a visit to the White House. This preference for vintage pieces in her personal wardrobe has also occasionally made its way into Rodrigo’s professional attire.
We take a look at Olivia Rodrigo fashion journey up to this point, beginning with her earliest days on the red carpet, when she wore jeans and sneakers, and ending with her wearing custom couture designs while accepting a Grammy Award.
Olivia Rodrigo’s Best Style
2016, Mattel Party
To attend a Mattel-hosted charity event, Olivia Rodrigo wore a casual outfit consisting of ripped jeans and sneakers. This event took place after the Disney premiere of Bizaardvark. In spite of the fact that her sense of style would undergo a significant transformation over the course of the subsequent five years, Rodrigo had already created her distinctive long, glossy haircut.
Everything Screening 2017,
Olivia Rodrigowore a ruffled miniskirt with red and green stripes and a blousy polka-dotted top to a movie premiere in 2017. This was Rodrigo’s way of experimenting with different patterns and colors.
2017, Pirates: Dead Men Tell No Tales Premiere
During the opening of the fifth installment of the Pirates of the Caribbean series, Olivia Rodrigo wore a dress that was icy blue and included metallic embroidery. This outfit was more in line with her current approach to fashion. The singer accessorized the midi dress with metallic sandals that matched the garment and a barely-there beauty look that included curls that cascaded over her face.
2018, Chinese American Film Festival
Olivia Rodrigo chose for a more traditional costume when she attended the Chinese American Film Festival. She wore a black fringe dress with sheer sleeves, and she combined it with a strong lip.
2019, High School Musical: The Musical: The Series Premiere
The premiere of High School Musical: The Musical: The Series was Olivia Rodrigo first large red carpet event, and it was the first time that everyone was looking specifically at her. As an alternative to wearing a dress, the singer opted to wear a black tulle skirt, which was a rather unusual choice.
In addition to the statement skirt, Rodrigo wore a white T-shirt, a gold choker necklace, and a new beauty style that comprised balayage curls, a black manicure, and a small cat eye. The floor-length silhouette had floral embroidery at the waist, which added a touch of glitter to the ensemble.
2021, The Brit Awards
Olivia Rodrigo traveled to London for the first time to attend the Brit Awards, which she attended few months after the publication of her debut track, “Drivers License.” Maria Grazia Chiuri, the creative director of Dior, was appointed to oversee the event, and the singer began the festivities by walking the red carpet wearing a gown that was neon yellow.
Rodrigo kept the strong colors going as she walked the stage to perform her hit track in a second Dior design: a custom red chiffon dress worn over red sequined shorts and a bra. The outfit was comprised of a strapless tulle material, and it was complemented with a black leather belt and platform sandals.
2021, At The White House
During the height of the pandemic, the White House sent an invitation to Olivia Rodrigo to function as a celebrity ambassador, with the purpose of encouraging young people to get vaccinated against the COVID-19 virus. As part of her position, the singer-songwriter met with President Biden and Dr. Anthony Fauci, who was serving as the chief medical advisor to the White House at the time.
She chose to wear an ensemble from the Chanel archive that was more traditional but still enjoyable. The pink tweed blazer and miniskirt that Olivia Rodrigo wore were initially featured in Chanel’s spring 1995 collection. She added finishing touches to the outfit by wearing a tiny black purse by Amina Muaddi and black ankle socks underneath Giuseppe Zanotti’s outrageously high white platforms.
2021, MTV Video Music Awards
While attending the 2021 MTV Video Music Awards, Olivia Rodrigo wore a sunset-colored gown from Versace’s spring 2001 couture line. This was yet another event that will go down in history. The stylists Chloe and Chenelle Delgadillo, who are siblings, chose the strapless silhouette for Olivia Rodrigo in peach satin and pink tulle.
To round off the ensemble, they added heritage butterfly earrings designed by Richard Kerr. Nevertheless, Rodrigo had a second outfit in store for him. Later on, he performed in a lilac and sky-blue dress that was custom-made by Marc Jacobs. He paired the dress with fishnet stockings and gloves that matched the dress. He won three trophies for his performance.
2022, Grammy Awards
For Olivia Rodrigo first Grammy Awards, Vivienne Westwood designed a unique black column gown—a match made in punk fashion heaven. With its combination of pink, purple, and black Swarovski crystal details, the corset dress produced an optical illusion. Rodrigo accessorized it with a lavender smoky eye, black opera gloves, a choker, and pink bejeweled necklaces. At the presentation, Rodrigo not only won three trophies but also looked stunning in a cream-colored Givenchy dress with a ruffled skirt, fishnet tights, platform boots, and a choker necklace.
2022, Rock & Roll Hall Of Fame Induction Ceremony
Even though Olivia Rodrigo sang Carly Simon’s popular song from the 1970s, “You’re So Vain,” at the 2022 Rock & Roll Hall of Fame induction ceremony, she looked like she was from the 1990s with her gray Shushu/Tong minidress. The dress was accessorized with sheer black garter socks, platform Mary Janes, and a choker necklace. It had a pleated skirt with cutouts down the side and back of the bodice.
2023, MTV Video Music Awards
The shimmering effect behind Olivia Rodrigo 2023 MTV VMAs outfit, which was designed especially for the singer by Ludovic de Saint Sernin in Paris, required 150,000 Swarovski crystals. Completely composed of crystal mesh, the dress required no extravagant embellishments; instead, it was accessorized with subtle makeup, neat hair, earrings, and a pair of silver rings that spoke the name of Rodrigo’s recently released second album, Guts. At the award presentation, Rodrigo not only sang two of her new tunes but also donned a much more relaxed red pleated skirt and bra, accessorizing it with leg warmers and sneakers.
2023, The Hunger Games: The Ballad Of Songbirds & Snakes Premiere
Olivia Rodrigo donned yet another glistening ensemble for The Hunger Games: The Ballad of Songbirds and Snakes’ Los Angeles premiere. This time, the singer—who wrote a song for the film—went with Rodarte’s black sequin outfit. Originally shown in white as part of the American luxury brand’s spring 2024 collection, Rodrigo’s personalized version retained the runway version’s hand-beaded pink and purple floral appliqués.