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.
2016, Mattel Party
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.
2017, Everything, Everything Screening
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.
2017, Pirates Of The Caribbean: Dead Men Tell No Tales Premiere
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.
2018, Chinese American Film Festival
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.
2019, High School Musical: The Musical: The Series Premiere
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 statement-skirt with a white T-shirt, gold choker necklace and a new beauty style that included balayage waves, a black manicure and a mini cat eye.
2021, The Brit Awards
Several months after the release of her debut single, “Drivers License,” Rodrigo headed to London for her first Brit Awards. Turning to Dior creative director Maria Grazia Chiuri for the occasion, the singer kicked things off on the red carpet in a fluorescent yellow gown. The strapless tulle dress was accessorized with a black leather belt and platform sandals, and Rodrigo kept the bold colors going when she took to the stage to perform her hit single in a second Dior design: a custom red chiffon dress worn over red sequined shorts and a bra.
2021, At The White House
In the midst of the pandemic, Rodrigo was invited by the White House to serve as a celebrity ambassador encouraging young people to get vaccinated against Covid-19. As part of her role, the singer-songwriter met with President Biden and then-chief White House medical advisor Dr. Anthony Fauci, opting for a more conservative (but still fun) ensemble from the Chanel archive. The pink tweed blazer and miniskirt Rodrigo sported originally appeared as part of Chanel’s spring 1995 collection, and she styled the look with a mini black handbag by Amina Muaddi and black ankle socks worn under sky-high white platforms by Giuseppe Zanotti.
2021, MTV Video Music Awards
It was another archive moment for Rodrigo at the 2021 MTV VMAs—this time in a sunset-colored gown from Versace’s spring 2001 couture collection. The strapless silhouette, which was crafted in peach satin and pink tulle, was selected for Rodrigo by sibling stylists Chloe and Chenelle Delgadillo, who added archive butterfly earrings by Richard Kerr to complete the look. But Rodrigo had a second look in store, later performing (and winning three awards) in a custom lilac and sky-blue dress by Marc Jacobs that was styled with matching gloves and fishnet stockings.
2021, Met Gala
Formal custom gowns and vintage dresses can be seen in abundance on the Met Gala red carpet, but Rodrigo decided to switch things up. For her first Met Gala, the “Good 4 U” singer arrived in a black lace catsuit by Saint Laurent. The sheer design included a feathered off-the-shoulder neckline and was styled with platform shoes, statement earrings and stacks of diamond bracelets. “I think it’s really fun that I’m not wearing a dress to my first Met,” Rodrigo said in a behind-the-scenes video for Vogue. “And I just think it looks so rock and roll, yet so sophisticated,” she added of the design, which was completed with a structured, slicked-back knot and floating black eyeliner.
2021, The Academy Museum Of Motion Pictures Opening Gala
A few weeks later, Rodrigo donned another daring Saint Laurent design when she arrived at the Academy Museum of Motion Pictures Opening Gala in a plunging black dress. The strapless design included a dramatic open neckline as well as a thigh-high slit, which Rodrigo chose to highlight by skipping the accessories entirely. A classic beauty pairing of a crisp red lip and low knot hairstyle pulled the whole look together.
2021, American Music Awards
Rodrigo closed out 2021 by winning the New Artist of the Year award at her first AMAs, dressing the part of celebrated pop princess in a lilac sequined halter gown by David Koma that was trimmed with ostrich feathers.
2022, Billboard Women In Music
Rodrigo embraced her punk side at Billboard’s annual Women in Music event, where she was honored with the Woman of the Year award. Wearing a bustier-style maxi dress from Area that included a tiered skirt and crystal-trimmed bodice, Rodrigo made the look her own by accessorizing with platform boots and several belts with crystal-trimmed buckles that matched the shoulder straps of her dress.
2022, iHeartRadio Music Awards
For the iHeartRadio Music Awards, Rodrigo went for a Y2K-themed look that started with a purple corset minidress and black latex leggings from Versace and was completed with platform shoes, floating black cat eyeliner and a snap clip-accessorized ponytail.
2022, Grammy Awards
A match made in punk fashion heaven; Vivienne Westwood created a custom black column gown for Rodrigo’s first Grammy Awards. The corset dress created an optical illusion with its mix of pink, purple and black Swarovski crystal detailing, which Rodrigo matched with a choker and pink bejeweled necklaces, black opera gloves and a shimmery lavender smoky eye. In addition to picking up three awards, Rodrigo also performed at the ceremony in a cream-colored dress by Givenchy that included a ruffled skirt and was styled with fishnet tights, platform boots and a choker necklace.
2022, Met Gala
For her second Met Gala, Rodrigo went all-out glam in a lilac mesh dress by Versace. The shimmering gown included draping at the shoulders, a thigh-high slit and an open back that flowed into a short train. In keeping with the monochromatic look, Rodrigo accessorized with sheer gloves, platform heels, diamond jewelry and oversized butterflies clipped into her volumized curls.
2022, MTV Movie & TV Awards
In a vintage first for Rodrigo, the singer-songwriter (and her then-stylists Chloe and Chenelle Delgadillo) turned to the Jean Paul Gaultier archive for this corseted black dress. The ankle-length design included criss-cross straps and the mini cone-shaped bra that Madonna made a part of her signature look in the ’80s. Of course, Rodrigo added a Y2K twist with strappy heels, a zig-zag-parted knot and crystal-spiked earrings from Outhouse Jewelry.
2022, High School Musical: The Musical: The Series Season 3 Premiere
For the season three premiere of the Disney+ show, High School Musical: The Musical: The Series, Rodrigo wore a black minidress by Nensi Dojaka. The strapless dress packed in plenty of design elements, thanks to its sheer paneling and skin-baring cutout that included a floral detail at the midriff. Rodrigo gave the look a rock and roll vibe with sheer tights, black platform shoes, a Dior choker necklace and a red lipstick with undone waves beauty combo.
2022, Givenchy Show
Though Rodrigo had spent over a year on every best-dressed list, she had yet to appear in the fashion front row. Givenchy marked the singer’s first official show (she had worn Givenchy earlier in the year for her Grammy performance), with Rodrigo attending the presentation for the French fashion house’s spring 2023 collection in Paris. Naturally, her look came courtesy of Givenchy, and it included a lace slip dress with a coordinating beige coat casually slung over her shoulders. Platform shoes, a slicked-back knot and a berry lip and manicure combo added a touch of edge to the otherwise classic look.
2022, Rock & Roll Hall Of Fame Induction Ceremony
Despite performing Carly Simon’s ‘70s hit “You’re So Vain” at the 2022 Rock & Roll Hall of Fame induction ceremony, Rodrigo sported a ‘90s-inspired look in her Shushu/Tong gray minidress. The dress, which included a pleated skirt and cutouts along the side and back of the bodice, was styled with sheer black garter socks, platform Mary Janes and a choker necklace.
2023, Grammy Awards
Armed with new stylist Danielle Goldberg, Rodrigo attended the 2023 Grammy Awards in a silk Miu Miu design that was entirely sheer. The black slip dress was worn with matching underwear, and Rodrigo accessorized with a Tiffany & Co. Elsa Peretti Bean Design necklace (also in black), as well as an assortment of smaller Tiffany & Co. earrings and rings.
2023, ‘Vanity Fair’ Oscar Party
Rodrigo was the ultimate glamour girl at the annual Vanity Fair Oscar party in a leopard print gown from Valentino’s pre-fall 2023 collection. The halter-style dress was entirely embellished with crystals, but the singer-songwriter added even more sparkle with Boucheron Vendôme Liseré diamond earrings.
2023, Met Gala
Rodrigo reinvented her Met Gala look once again, this time in a custom Thom Browne dress that appeared to put her signature ‘90s grunge spin on a ‘60s classic: Audrey Hepburn in My Fair Lady. In keeping with the gala’s theme, the singer’s gown was a black and white tweed design that paid tribute to designer Karl Lagerfeld, but the strapless neckline was also embellished with silk camellia flowers, another homage to Lagerfeld’s time at Chanel. Lorraine Schwartz diamond earrings and rings that were trimmed with black onyx matched the black-and-white theme, and Rodrigo’s beauty look centered around Hepburn-inspired baby bangs.
2023, MTV Video Music Awards
It took 150,000 Swarovski crystals to create the shimmery effect behind Rodrigo’s 2023 MTV VMAs dress, which was custom-made for the singer by Ludovic de Saint Sernin in Paris. Made entirely of crystal mesh, the gown didn’t require any over-the-top accessories, and was instead paired with minimal makeup, sleek hair, earrings and a set of silver rings that spelled out the title of Rodrigo’s just-released second album, Guts. Rodrigo also performed two of her new singles at the award show, wearing a much more casual red pleated skirt and bra, which she styled with sneakers and leg warmers.
2023, The Hunger Games: The Ballad Of Songbirds & Snakes Premiere
For the Los Angeles premiere of The Hunger Games: The Ballad of Songbirds and Snakes, Rodrigo wore another sparkly number. This time around, the singer, who contributed a song to the movie, opted for a black sequin design by Rodarte. The column gown was originally part of the American luxury brand’s spring 2024 collection in a white color, but Rodrigo’s custom take still included the hand-beaded pink and purple floral appliqués from the runway version.
2023, GQ Men Of The Year
Rodrigo put aside the floor-length gowns for GQ’s Men of the Year party in favor of a fringe minidress from Tom Ford’s spring 2024 collection. The strapless design got just the tiniest pop of color with the gold hardware piece along the neckline, and Rodrigo added matching gold hoop earrings, gold rings and a beauty look that included her go-to black cat eye and a tousled updo with face-framing pieces.