As the Filipino American singer enters her romantic era, take a look at Olivia Rodrigo’s best fashion moments.
When Olivia Rodrigo released “Drivers License” in 2021, the Filipino American singer seemed to have a clear grasp of her sound and aesthetics. Since then, we’ve watched her grow through each of her eras: the youthful, punk-grunge aesthetic of Sour and the rebellious teenage spirit of Guts. In 2024, “So American” was released as part of the deluxe edition of her second studio album, Guts (Spilled), the first love song in her entire discography.
Now, as she returns with her third album, you seem pretty sad for a girl so in love, it seems that we’ll see more of her romantic side, kicking off the era with a new love song, “drop dead.” As she trades her fishnets for knee-high socks and frills, take a look back at some of her best looks through the years.
Sour Era (2021–2022)
For her debut album, Rodrigo leaned in heavily into the Y2K-inspired punk-grunge aesthetics with plaid skirts, corset tops, combat boots, and signature purple hues. Key elements of her Sour aesthetics were plaids, corsets and bustiers paired with mini skirts and trousers, mirroring 2000s pop-punk trends in teenage rebellious fashion. During this era, she also frequently used archival pieces, such as Chanel and Versace.
Of her Sour Era looks, perhaps one of the most talked about is her FANCi mini-dress and matching gloves at the premiere of driving home 2 u (a SOUR film).
And of course, who could forget her 2022 Met Gala look? The pop singer-songwriter wore a lavender satin Versace gown with a cowl neckline, sheer gloves, and purple butterflies in her hair.
Guts Era (2023–2025)
For her sophomore album, Guts, her aesthetics continued the edgy and grunge-inspired styles, featuring custom plaids, sparkling mini skirts, and archival pieces. While her colors still focused on purple hues, red also became a key part of her aesthetic, primarily seen in varying types of bodysuits.
Her Guts world tour custom bodysuits are a fan favorite, usually in red or black sparkles, paired with fishnets or star-patterned tights.
Another fan favorite is her 2025 Grammys look, where she wore a vintage black Versace gown from the Spring/Summer 2000 collection, featuring dramatic cutouts, a halter neck with a keyhole bust, and a completely backless design.
You seem pretty sad for a girl so in love Era (2026–present)
In her current era, the pop artist ditches her purple hues for softer, romantic palettes. For her third album, you seem pretty sad for a girl so in love, she abandons her pop-punk angst, as seen in her recently released “drop dead” music video. Filmed at the Palace of Versailles, her music video look is described as a “Gen-Z-meets-Marie Antoinette” look, styled by Chloe and Chenelle Delgadillo.
The key outfit features a baby-blue chemise and bloomers from Chloé pre-fall 2026, along with a pearl-studded mini dress associated with Jane Birkin.
Babydoll dresses seem to be coming back into fashion, with Rodrigo being spotted wearing a custom babydoll dress by designer Jane Doe at Feel Karaoke in Los Angeles. And instead of Doc Martens, the star wore double-strap Miu Miu pumps.
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