Olivia Rodrigo’s wardrobe isn’t rage bait. It’s researched

By Chelsey Sanchez

It’s never easy for pop stars to introduce their next era. If they cling too closely to what has been done in the past, critics may grumble over a lack of innovation. If they veer too far from what fans know and expect, they risk losing the base that gave them a platform in the first place. For Olivia Rodrigo, the new “You Seem Pretty Sad for a Girl so in Love” era has mostly relied on — as she sings in the lead single, “drop dead” — her own feminine intuition.

The 23-year-old’s third studio album, released this month, ushers in perhaps the most exciting phase of her career yet, one where both her style and sound are maturing in tandem.

The 13-track record chronicles the lifespan of a relationship, from the exuberance of initial infatuation to the whiplash of begging for affection from a partner that was once so easily enamored. It’s already earned Rodrigo her third consecutive No. 1 on the Billboard 200 albums chart. She kept the momentum going Monday with the announcement of Daisy Chain Fields, a new music festival featuring an all-women lineup — including Chappell Roan, Doechii, Bikini Kill and Katseye — with proceeds going towards women advocacy organizations. The event takes after Lilith Fair, the groundbreaking ‘90s feminist festival founded by Sarah McLachlan, who will also make a special guest appearance, along with Stevie Nicks and Karen O.

Rodrigo’s previous two albums,“Sour” (2021) and “Guts” (2023), were industry-shakers in their own right. Songs like “Drivers License” and “Vampire” demonstrated her talent for writing breakup ballads, while hits like “Good 4 U” and “Get Him Back” showcased her proficiency in ‘90s punk rock — an arena of music which has become her signature sonic playground. Up until now, Rodrigo’s style reflected that musical predilection, with the singer’s rotation of plaid miniskirts and platform boots often landing as a hybrid mix between Gwen Stefani and Cher Horowitz. Rodrigo’s eras have clearly defined color palettes too; her first two albums were synonymous with a spunky purple hue, while “You Seem Pretty Sad” has subtly shifted to a definitively girly powdery pink.

If the job of a debut album is to introduce an artist to the world, while a sophomore album reinforces their reputation, then a third album offers a channel for artists to expand beyond the familiar tricks and peculiarities that shot them to fame in the first place. In Rodrigo’s case, “You Seem Pretty Sad” mostly ditches the pop punk and alt-rock references and, instead, borrows sounds that defined the ‘80s. Think New Order, or post-punk flourishes from The Cure (the English band’s frontman, Robert Smith, even makes an appearance on the album’s B-side track, “What’s Wrong with Me”). Rodrigo’s wardrobe naturally followed suit.

Her deft use of fashion during the “You Seem Pretty Sad” rollout does more than allow Rodrigo to play dress up — it also functions as a vehicle for her artistry. Gone are the Mary Jane Dr. Martens and schoolgirl plaid skirts. Working with sister stylist duo Chloe and Chenelle Delgadillo, Rodrigo has reconstructed her signature looks to feel softer and more grown-up, with outfits drawing from fashion references just as diverse as her musical taste.

Anatomy of a new era

The new album “ends up pulling a little bit from ‘80s new wave, but her look isn’t really going ‘80s new wave,” said music journalist Brittany Spanos of Rodrigo’s evolving sound and style. “Whereas she’s been pulling from grungier ‘90s looks for her last two album cycles, this one she expanded more into the hyper femme versions of it.”

To shape this era’s “femme palette,” Rodrigo has worn a mix of shift dresses reminiscent of ‘60s mod, ballet flats from the ‘70s-founded shoe brand Repetto, Y2K-style jeans paired with peep-toe heels, and modern riffs on the twee aesthetic. The music video for the album’s first single, “Drop Dead,” featured Rodrigo in two outfits: a replica of a crochet dress that Jane Birkin wore in the 1975 French film, “Catherine & Co,” and a pink-and-blue nightgown set from Chloé’s pre-fall 2026 collection — the latter of which looks like it could have been taken straight from the costume department of Sofia Coppola’s “Marie Antoinette.”

“I think Olivia knows how to work a reference in a more profound sense than many pop stars,” stylist and trends spokesperson at social shopping app Depop, Gabriella Karefa-Johnson, said over email. (Depop serves as one of the official partners of Rodrigo’s Daisy Chain Fields.) “When I think about her boho, and early aughts, and Jane Birkin nods, what is clear to me is that there is no real aesthetic throughline. The reference is more a state of being and a message of liberation — these are all aesthetics that connote women at their wildest and most free. That’s what her music is about, so why not also look that way?”

Rodrigo’s recent wardrobe contributes to the album’s worldbuilding, but her new style hasn’t been formed in a vacuum, either. “She knows how young people are dressing right now — she is one!” Karefa-Johnson said.

In the last three months alone, Depop searches for babydoll dresses have increased by 144%, Y2K low- rise jeans by 102%, and peep toe heels by 108%, according to the platform. Rodrigo’s other beloved trends, like vintage mod and indie sleaze, are also on the rise on the site.

But the relationship between Rodrigo’s wardrobe choices and this year’s trend cycles is also symbiotic.

“You can’t really have the history of popular music without the history of fashion,” Spanos said. “It’s completely braided together. Artists, genres and things like music eras have always influenced and formed trends in fashion, and vice versa.”

Why fashion references matter

Then the babydoll-sized elephant walked into the room.

Shortly after Rodrigo released her new album’s lead single, the pop star found herself at the center of a media maelstrom. A puff-sleeved babydoll dress she wore onstage during a Spotify concert in Barcelona saw some on social media accused Rodrigo of promoting a hypersexualized childlike aesthetic. Public outrage over how a female pop star dresses has, of course, recurred long before Rodrigo became a household name. The past few decades saw similar degrees of vitriol lobbed against the likes of Miley Cyrus, Britney Spears and Christina Aguilera.

Rodrigo pushed back against the outcry in an interview with the New York Times in May. Her outfit was reminiscent of feminist riot grrrl “heroes” Kathleen Hanna and Courtney Love, she said, adding, “You shouldn’t be responsible for some guy sexualizing you in some way that was never your intention.”

“I think some of the confusion was a feeling of disconnect between the sound and look,” said Spanos, who wrote about the controversy in an essay for The Cut. While the tone and subject matter of “You Seem Pretty Sad” may not exactly emulate the punk social commentary found in the discography of Rodrigo’s riot grrrl heroes, the babydoll dress still plays a role in how she wants to represent this new chapter of her career. “There’s a softness and a vulnerability,” said Spanos of Rodrigo’s latest album, that led her to “embrace these femme silhouettes and structures that have a little bit of an edge to them.”

Independent music critic Molly Mary O’Brien noted how the early-to-mid-’90s period that produced the original iteration of pop-punk fashion, and the current moment Rodrigo now operates within, are vastly different. “We have this very long lineage of female musicians subverting sexual expectations or just expectations of femininity,” O’Brien said. “It’s almost a symbol of how far women in the music industry have come, in a sense, that in the ‘90s grunge was an alternative movement that went mainstream. I feel like Rodrigo is maybe signifying this in her clothing… There is this continual push-pull between alternative and mainstream that she’s almost trying to thread the needle with.”

The way celebrities employ fashion references in their wardrobes is no accident, said Karefa-Johnson. “We need to be thinking critically and engaging with the complexity beneath the visual surface of a trend or reference,” she added. “The most compelling fashion references use history as a point of departure — they create friction by rubbing the future against the past. A reference shouldn’t be a blueprint but rather a jumping off point from which to explore something new.”

An era of experimentation

Rodrigo follows in the footsteps of other pop juggernauts who use sartorial Easter eggs to tease new musical eras. While Taylor Swift often gets credit for popularizing the notion of era reinventions, artists have played with their visuals to communicate and market new album cycles for decades — just look at Beyoncé, Madonna, David Bowie and The Beatles.

The broad genre of pop also gives artists room to experiment, said O’Brien, adding that audiences these days are well aware of the concept of eras and understand artists will go through multiple ones throughout their careers.

“The easier you can describe something, the easier it is you can sell it,” O’Brien said. “America loves a teen pop star, and then we love ripping them to shreds when they have any sign of agency or autonomy… The times change, but there is that impulse to keep questioning the integrity of young female performers.”

If anything, the dichotomy between the pop star who prances around Versailles in a sheer nightie and the pop star who stomps onstage in knee-high combat boots feels completely authentic and intentional. Just like the two halves of “You Seem Pretty Sad,” Rodrigo’s wardrobe plays with the thin threshold between falling in love and breaking your heart.

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