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Olivia Rodrigo Has Cheeky Reaction to Marilyn Monroe-Style Wardrobe Malfunction During Recent Performance

Rodrigo performed her latest hits at the Grammy Museum on Sept. 1

Olivia Rodrigo performing at the 2025 Glastonbury Festival
Credit: Kevin Mazur/Getty

NEED TO KNOW

  • Olivia Rodrigo recovered from a cheeky wardrobe malfunction while performing at the Grammy Museum on Sept. 1
  • The “Drop Dead” singer was filmed handling the faux pas in a video captured by an attendee and shared to TikTok
  • Rodrigo discussed her new album You Seem Pretty Sad for a Girl So in Love at the event just days after pulling off her first Daisy Chain Fields festival on Aug. 29

Olivia Rodrigo never looked so cool, even when handling a wardrobe malfunction.

The 23-year-old pop star has had a whirlwind summer between debuting her third album, You Seem Pretty Sad for a Girl So in Love, and pulling off her first-ever music festival. To cap off a busy few months, Rodrigo appeared at Los Angeles’ Grammy Museum on Sept. 1 for an event spotlighting her latest record, plus the opening of the “Olivia Rodrigo: the cure unraveled” exhibit.

Rodrigo took the stage for a discussion and a performance, during which a fan captured her handling a slight outfit faux pas with grace while singing “Drop Dead.”

Olivia Rodrigo performing on ‘Jimmy Kimmel Live!’ on June 10, 2026
Credit: Randy Holmes/Disney via Getty

In a video shared to TikTok, the Grammy winner is seen performing on the venue’s Ray Charles Rooftop Terrace when the skirt of her minidress gets blown up by the wind, revealing her shorts underneath. She laughs off the innocent gaffe before continuing the song, but while holding her dress in place.

“This was so cute,” the attendee wrote across the clip.

Rodrigo’s You Seem Pretty Sad for a Girl So in Love was released on June 12, and its hits were brought to the first Daisy Chain Fields festival on Aug. 29, held two months after it was first announced.

The not-for-profit event was fronted by a women-led lineup of performers, including Chappell Roan, Sarah McLachlan, Doechii and Rodrigo, who was joined by musical icon Stevie Nicks. “I actually feel like it’s my calling in some weird way,” Rodrigo told Pitchfork about the festival in June. “I…have had this dream to do this festival for a really long time.”

Olivia Rodrigo performing the Spotify x FC Barcelona Billions Club Live show on May 8, 2026
Credit: Xavi Torrent/Getty

“I just feel like we need something really positive to do and see, and young girls need awesome role models who are supporting other women and who are engaging in something that’s really joyful and musical and community-oriented,” she added.

Daisy Chain Fields had raised $10 million to be donated to 10 nonprofit organizations, but the amount was doubled with a donation from Melinda French Gates.

“Melinda is one of the most inspiring women I’ve ever met,” Rodrigo said on stage. “She’s devoted her life to empowering women and girls that would’ve otherwise been forgotten. She’s generous and brave and has done so much good in this world, and I am totally floored because as well as being in attendance here tonight, she’s pledged to double every dollar that we made here today.”



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