Olivia Rodrigo uses fashion to tell the story of her new era

It's never easy for pop stars to introduce a new phase in their career. If you stick too closely to what you've done in the past, you may hear criticism for the lack of innovation. If they stray too far from what fans know and expect, they run the risk of losing the base that gave them prominence. In Olivia Rodrigo's case, the new era of "You Seem Pretty Sad for a Girl so in Love" relies primarily - as she sings on her debut single, "Drop Dead" - on her own feminine intuition.

The 23-year-old artist's third studio album, released this month, ushers in perhaps the most exciting phase of her career to date, in which her style and sound mature side by side.

The album, with 13 tracks, follows the cycle of a relationship, from the euphoria of initial passion to the impact of begging for affection from a partner who was previously easily in love.

The album has already earned Rodrigo her third consecutive first place on the Billboard 200 chart. She kept the momentum going on Monday by announcing Daisy Chain Fields, a new music festival with an all-female line-up - including Chappell Roan, Doechii, Bikini Kill and Katseye -, with proceeds going to women's rights organizations.

The event is inspired by Lilith Fair, the pioneering 1990s feminist festival created by Sarah McLachlan, who will also make a special appearance, alongside Stevie Nicks and Karen O.

Rodrigo's two previous albums, "Sour" (2021) and "Guts" (2023), had already shaken the music industry. Tracks like "Drivers License" and "Vampire" showed his talent for composing ballads about breakups, while hits like "Good 4 U" and "Get Him Back" highlighted his skill in 1990s punk rock - a musical universe that became his main sonic brand.

Until now, her style has reflected this preference, with plaid miniskirts and platform boots that look like a cross between Gwen Stefani and Cher Horowitz. Rodrigo's eras also always had well-defined color palettes: the first two albums were associated with vibrant purple, while You Seem Pretty Sad discreetly migrated to a distinctly feminine light pink.

If the function of a debut album is to introduce an artist to the world, and the function of the second is to consolidate their reputation, the third offers the opportunity to expand beyond the formulas and characteristics that made them famous.

In Rodrigo's case, "You Seem Pretty Sad" practically abandons references to pop punk and alternative rock and, instead, incorporates sounds that marked the 1980s. Think of New Order or the post-punk elements of The Cure (the English band's lead singer, Robert Smith, even participates in the track "What's Wrong with Me", side B of the album). Naturally, the singer's wardrobe followed this change.

The thoughtful use of fashion during the promotion of "You Seem Pretty Sad" does more than allow Rodrigo to experiment with new looks - it also functions as an artistic tool. Out come the Mary Jane shoes from Dr. Martens and the plaid schoolgirl skirts. Working with sister and stylist duo Chloe and Chenelle Delgadillo, Rodrigo reconstructed her signature looks to appear more delicate and mature, with looks inspired by fashion references as diverse as her musical taste.

Anatomy of a new era
The new album "ends up incorporating a bit of 1980s new wave, but its look doesn't exactly follow that aesthetic", said music journalist Brittany Spanos about the evolution of Rodrigo's sound and style. "Whereas in her previous two album cycles she looked to more grunge 1990s visuals for references, this time she expanded that into more hyper-feminine versions of that aesthetic."

To build the "feminine palette" of this new phase, Rodrigo opted for a combination of straight dresses inspired by the mod fashion of the 1960s, sneakers from Repetto - a brand founded in the 1970s -, 2000s style jeans combined with peep toe shoes and contemporary reinterpretations of the twee aesthetic.

In the music video for the album's first single, "Drop Dead", Rodrigo appears in two outfits: a replica of a crochet dress worn by Jane Birkin in the French film "Catherine & Co" (1975) and a pink and blue sweater set from Chloé's pre-fall 2026 collection - the latter with a look that could have come straight out of Sofia Coppola's Marie Antoinette costume.

"I think Olivia knows how to work references in a deeper way than many pop stars," said Gabriella Karefa-Johnson, stylist and trends spokesperson for the fashion shopping app Depop, via email. (Depop is one of the official partners of Rodrigo's Daisy Chain Fields festival.)

"When I think about the references to boho style, the 2000s and Jane Birkin, what becomes clear to me is that there is no single aesthetic thread. The reference is more of a state of mind and a message of liberation - all of these aesthetics refer to women in their freest and most intense moments. That's what her music is about, so why shouldn't she dress that way too?"

Rodrigo's recent wardrobe helps build the album's universe, but his new style didn't emerge in isolation either. "She knows how young people are dressing today - after all, she is one of them!" said Karefa-Johnson.

In the last three months alone, searches for babydoll dresses have increased by 144% on Depop, while searches for low-rise jeans from the 2000s have grown by 102%, and for peep-toe shoes, by 108%, according to the platform. Other trends that Rodrigo loves, such as vintage mod fashion and indie sleaze, are also trending on the site.

But the relationship between the singer's wardrobe choices and this year's fashion trends is symbiotic.

"You can't tell the story of popular music without telling the story of fashion," said Spanos. "The two are completely intertwined. Artists, musical genres and career stages have always influenced and shaped fashion trends, and the opposite also happens."

Why fashion references matter
That's when the babydoll dress became the elephant in the room.

Shortly after Rodrigo released the first single from her new album, the singer found herself at the center of a media storm. A babydoll dress with puffed sleeves that she wore during a show promoted by Spotify in Barcelona led some people on social media to accuse her of promoting a childish and hypersexualized aesthetic.

Public outrage over the way a pop star dresses, however, existed long before Rodrigo became a household name. In recent decades, artists like Miley Cyrus, Britney Spears and Christina Aguilera have faced similar backlash.

Rodrigo countered the criticism in an interview with The New York Times in May. According to her, the costume made reference to the "heroines" of the riot grrrl feminist movement, Kathleen Hanna and Courtney Love. "You shouldn't be held responsible for some man sexualizing you in a way that was never his intention," she said.

"I think part of the confusion came from a sense of disconnect between the sound and the visuals," said Spanos, who wrote about the controversy in an article for The Cut magazine. While the tone and themes of "You Seem Pretty Sad" don't exactly replicate the social commentary present in Rodrigo's discography of riot grrrl heroines, the babydoll dress still plays an important role in how she wants to represent this new chapter in her career.

"There's a softness and a vulnerability," said Spanos of Rodrigo's new album, which led her to "embrace feminine silhouettes and structures that also have a bit of edge."

Independent music critic Molly Mary O'Brien observed that the period between the early and mid-1990s - which gave rise to the first wave of pop punk fashion - and the current moment, in which Rodrigo is building his career, are very different.

"We have a long history of women in music subverting sexual expectations, or simply expectations related to femininity," said O'Brien.

"In a way, it's almost a symbol of how far women in the music industry have come. In the 1990s, grunge was an alternative movement that ended up becoming popular. I think Rodrigo is perhaps signaling that through her clothing... There's this constant movement between alternative and mainstream, and she seems to be trying to balance those two things."

The way celebrities use fashion references in their outfits doesn't happen by chance, said Karefa-Johnson.

"We need to think critically and understand the complexity that exists behind the visual surface of a trend or a reference," he added. "The most interesting fashion references use history as a starting point - they create friction by bringing the future into contact with the past. A reference should not serve as a model to be copied, but as a starting point for exploring something new."

An era of experimentation
Rodrigo follows in the footsteps of other pop giants who use visual references in their costumes to suggest new phases of their career. Although Taylor Swift is often credited with popularizing the concept of "eras", artists have been using the aesthetic to communicate and promote new album cycles for decades - look no further than Beyoncé, Madonna, David Bowie and the Beatles.

The pop genre itself also offers artists room to experiment, O'Brien said, adding that today's audiences are already quite familiar with the idea of "eras" and understand that artists go through several of them throughout their careers.

"The easier it is to describe something, the easier it is to sell it," said O'Brien. "America loves a teenage pop star and then loves to destroy her as soon as she shows any sign of autonomy or independence... Times change, but there continues to be this impulse to question the integrity of young female artists."

Ultimately, the dichotomy between the pop star who parades around Versailles in a sheer nightgown and the performer who steps on stage in knee-high combat boots feels completely authentic and intentional. Just like the two halves of You Seem Pretty Sad, Rodrigo's wardrobe explores the fine line between falling in love and having your heart broken.

Source: CNN