Olivia Rodrigo handled a windy-day wardrobe moment the way most of us wish we could: she laughed and kept singing.
The 23-year-old performed on the Ray Charles Rooftop Terrace at the Grammy Museum in Los Angeles on Sept. 1, at an event celebrating her new album and the opening of the exhibit Olivia Rodrigo: the cure unraveled. During “Drop Dead,” a gust blew up the skirt of her minidress, showing the shorts underneath. A fan’s TikTok shows her laughing it off and holding her dress down for the rest of the song, in a moment that recalls Marilyn Monroe’s famous subway-grate scene.
A huge summer for Rodrigo
- New album: Her third record, You Seem Pretty Sad for a Girl So in Love, came out June 12.
- Her own festival: Rodrigo launched Daisy Chain Fields on Aug. 29, with a women-led lineup that included Chappell Roan, Sarah McLachlan and Doechii. Stevie Nicks joined her on stage. She has said the event, built around women supporting women, felt like a calling.
- Giving back: The festival raised $10 million for 10 nonprofits, and Melinda French Gates pledged to match it, doubling the total.
Our take
Plenty of stars would have stopped the show, but Rodrigo stayed relaxed, and fans loved it. It fits the image she’s built this year: confident, down to earth and focused on lifting up other women, as she did with her festival.

