The Coolest ’90s Style From Lollapalooza’s Early Years

The Coolest ’90s Style From Lollapalooza’s Early Years

Though we are “officially” in the midst of a Y2k style renaissance, you have to admire the persistence of ’90s style: Baby tees, wide leg jeans, and, yes, even those Adidas Sambas everyone’s wearing these days all have their sartorial roots in the tail end of the 20th century. Ahead of the Lollapalooza festival kicking off this weekend in Chicago, we thought we’d take a stroll through memory lane and check out what all the performers were wearing during what was arguably its heyday. We had forgotten the penchant for psychedelic polyester shirts (remember when ’90s style did ’70s style?), and how women just couldn’t say no to the slip dress.

Before the internet, when you weren’t constantly getting updates about what your favorite musician or celebrity was getting into or what they were like (beyond whatever clues you uncovered from CD booklets and music videos), seeing images of them performing live was an important insight into their personalities. They also provided a healthy dose of style inspiration (and FOMO, as I did not grow up in a Lollapalooza-adjacent place).

It didn’t matter that I never went, its influence was inescapable. Did I own a silver polyester baby tee with a striking resemblance to the dress D’arcy of Smashing Pumpkins performed in at Lollapalooza in Chicago? Yes. And did I have the below photo of Courtney Love from a 1995 Lollapalooza performance hanging on my bedroom wall? Of course I did, thank you Circus magazine! And did I also want a Built by Wendy guitar strap like the one she had more than anything in the world? Also yes, but I recently found out Wendy still makes them so that’s one thing off the bucket list! So blast open a Crystal Pepsi or a Zima, put on your favorite mixtape, and enjoy the 36 most iconic images of Lollapalooza ’90s style.

Perry Farrell of Jane’s Addiction wearing an elegant suit accessorized with a hat and a bottle of wine. Lollapalooza 1991

Ebet Roberts/Getty Images