Olivia Rodrigo popped up on stage at Lollapalooza this year, and honestly, nobody saw it coming.
She joined The Smashing Pumpkins during their headlining set in Chicago on July 31, belting out “Thirty-Three” alongside Billy Corgan like she’d rehearsed it for weeks. The whole thing felt spontaneous but also kind of perfect, y’know?
For the surprise gig, Rodrigo pulled out a seriously rare piece: a vintage Balenciaga minidress straight from Nicolas Ghesquière’s spring/summer 2006 collection. Semi-sheer, lace-up, covered in ruffles with those little cap sleeves—it’s the kind of dress that fashion nerds would recognize instantly.
She didn’t stop there either. Underneath the dress she wore white shorts, then added knee-high socks and classic Mary Jane shoes. Her hair got the full treatment too, braided into this elaborate updo that took the whole look up a notch.
Here’s a fun fact—”Thirty-Three” came out in 1995, off Mellon Collie and the Infinite Sadness, which means the song existed a full eight years before Rodrigo was even born in 2003. Wild timing, honestly. Yungblud also made a surprise cameo that same night, so the Pumpkins clearly went all out for their hometown crowd.
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Rolling Stone called her appearance one of the standout moments of the entire festival, and Corgan himself introduced her as a “very, very special guest” while the crowd went nuts.
We kind of love that Rodrigo keeps pulling these random surprise appearances out of nowhere. 🎸
Babydoll dresses have basically become her signature at this point. She explained to Vogue back in May that she’s always been drawn to that style, name-dropping Courtney Love and Kat Bjelland from the riot grrrl scene as major inspirations—she loved how they just “owned” the look.
That style choice actually sparked some backlash earlier this year, which Rodrigo addressed head-on during an episode of The New York Times’ “Popcast.” She pointed out something kind of messed up: she’s worn way more revealing stuff onstage—like a sparkly bra with tiny shorts—and nobody batted an eye. But put her in a fully-covered dress that some people called “childlike,” and suddenly it’s controversial?
She dug into why that double standard exists too, saying girls get taught from a young age that covering up or dressing a certain way means they’re somehow responsible if someone sexualizes them. Rodrigo said she never felt sexy in the dress at all—she felt like she was channeling Kathleen Hanna or Courtney Love, artists she genuinely admires.
The whole situation, she admitted, left her feeling pretty frustrated and upset.