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

A collage of live performers from Lollapalooza
s first decade.
Photos: Getty Images (George Clinton, Courtney Love, Trent Reznor, Tricky) and Alamy Stock Photo (Sinéad O’Connor)

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 Janes Addiction wearing an elegant suit accessorized with a hat and a bottle of wine. Lollapalooza 1991

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
Adam Yauch and Adam Horowitz of the Beastie Boys in matching widelegged pants and shortsleeve buttondowns. Lollapalooza 1994

Adam Yauch and Adam Horowitz of the Beastie Boys in matching wide-legged pants and short-sleeve button-downs. Lollapalooza 1994

Ebet Roberts/Getty Images
Sinad O
Connor performs during Lollapalooza.

Sinéad O’Connor in an easy-ribbed top and red jeans. Lollapalooza 1995

Photo: Jeremy Hogan / Alamy Stock Photo
An animal print tank matches L7s Donita Sparkss Flying V guitar. Lollapalooza 1994

An animal print tank matches L7’s Donita Sparks’s Flying V guitar. Lollapalooza 1994

Ebet Roberts/Getty Images
Smashing Pumpkinss Billy Corgan in a psychedelic tee . Lollapalooza 1994

Smashing Pumpkins’s Billy Corgan in a psychedelic tee (and hair!). Lollapalooza 1994

Tim Mosenfelder
The most dapper printmixing on Nick Cave . Lollapalooza 1994

The most dapper print-mixing on Nick Cave (and the Bad Seeds). Lollapalooza 1994

Ebet Roberts
Timothy Leary in a high school art teacher look. Lollapalooza 1993

Timothy Leary in a high school art teacher look. Lollapalooza 1993

Photo: Tim Mosenfelder/Getty Images
Lush during Lollapalooza 1993  Jones Beach at Jones Beach Theater in Wantagh New York

Lush’s Miki Berenyi in the classic summer uniform of cut-off lumberjack plaid shirt and jorts. Lollapalooza 1993

Photo: Steve Eichner
Metallicas Kirk Hammett in a very Gucciesque ensemble of lacy shirt and leather pants. Lollapalooza 1996

Metallica’s Kirk Hammett in a very Gucci-esque ensemble of lacy shirt and leather pants. Lollapalooza 1996

Patti Ouderkirk
Tricky performs as part of the Lollapalooza Tour 1997 at Shoreline Amphitheatre on August 16 1997 in Mountain View...

Tricky’s tenderly illustrated button-down shirt and trousers feel very proto-Bode, and his touring bass player Carrie Melbourne is showcasing a peak ’90s outfit of camo mesh dress and braids. Lollapalooza 1997 

Photo: Tim Mosenfelder/Getty Images
Green Days Mike Dirnt in the custodian uniform shirt  a 90s fashion musthave. Lollapalooza 1994

Green Day’s Mike Dirnt in the custodian uniform shirt (complete with someone else’s name patch), a ’90s fashion must-have. Lollapalooza 1994

Tim Mosenfelder/Getty Images
Snoop Dogg in another classic uniform shirt West Coast fit. Lollapalooza 1994

Snoop Dogg in another classic uniform shirt West Coast ’fit. Lollapalooza 1994

Bob Berg/Getty Images
Siouxsie Sioux of Siouxsie and the Banshees performing during Lollapalloza at Shoreline Amphitheater in Mountain View...

Siouxsie Sioux of Siouxsie and the Banshees in a look that should likely inspire at least one Chopova Lowena collection in the future. Lollapalooza 1991

Photo: Tim Mosenfelder/Image Direct
Kim Gordon performs during Lollapalooza.

Sonic Youth’s Kim Gordon in the essential ’90s style building blocks: a tank, an A-line miniskirt and peep-toe Mary Jane clogs. Lollapalooza 1995

Photo: Jeremy Hogan / Alamy Stock Photo
Layne Staley of Alice in Chains in a herringbone and supremely 90s paisleyprint tie. Lollapalooza 1993

Layne Staley of Alice in Chains in a herringbone and supremely ’90s paisley-print tie. Lollapalooza 1993

John Lynn Kirk/Getty Images
Moby wearing Moby . Lollapalooza 1995

Moby wearing Moby (before the Teany days). Lollapalooza 1995

Ebet Roberts/Getty Images
Trent Reznor of Nine Inch Nails performs as a part of at Lollapalooza 1991 at Shoreline Amphitheatre on July 26 1991 in...

Nine Inch Nails’s Trent Reznor wearing a “Now I’m Nothing” Nine Inch Nails tee, (except, of course, he’s everything). Lollapalooza 1991

Photo: Tim Mosenfelder/Getty Images
Arrested Developments Speech wearing an A Tribe Called Quest tee. Lollapalooza 1993

Arrested Development’s Speech wearing an A Tribe Called Quest tee. Lollapalooza 1993

Tim Mosenfelder/Getty Images
Richard Ashcroft of The Verve wearing a Funkadelic “Free Your Mind” tee autographed by George Clinton. Lollapalooza 1994

Richard Ashcroft of The Verve wearing a Funkadelic “Free Your Mind” tee autographed by George Clinton. Lollapalooza 1994

Steve Eichner
Pavements Stephen Malkmus repping the obscure literary journal The Minus Times on his Tshirt because of course he was....

Pavement’s Stephen Malkmus repping the obscure literary journal The Minus Times on his T-shirt, because of course he was. Lollapalooza 1995

Tim Mosenfelder/Getty Images
Beck in a striped polo shirt and corduroys looking like every downtown skater dude ever. Lollapalooza 1995

Beck in a striped polo shirt and corduroys looking like every downtown skater dude ever. Lollapalooza 1995

Photo: Photo by Kevin Mazur/WireImage
James Iha of Smashing Pumpkins in a plain ringer tee to better show off his shredding skills . Lollapalooza 1994

James Iha of Smashing Pumpkins in a plain ringer tee to better show off his shredding skills (and let his signature bleached-chunks hairdo shine). Lollapalooza 1994

Steve Eichner
Anthony Kiedis of Red Hot Chili Peppers performs at Lollapalooza

When you can’t wear a slogan tee because you're perpetually topless…. Red Hot Chili Pepper’s Anthony Kiedis in slogan shorts (they say “YOUR ASS” in the back). Lollapalooza 1991

Photo: Steve Eichner/Getty Images
D
arcy Wretzky of The Smashing Pumpkins performs during Lollapalooza at Shoreline Amphitheatre on August 28 1994 in...

Smashing Pumpkins’s D’arcy Wretzky is a silver rocket in a metallic slip. Lollapalooza 1994

Photo: Tim Mosenfelder/Getty Images
Blind Melons Shannon Hoon loading up on accessories. Lollapalooza 1993

Blind Melon’s Shannon Hoon loading up on accessories. Lollapalooza 1993

Steve Eichner/Getty Images
James Hetfield of Metallica wearing a silver choker necklace that matches his lowslung chain belt. Lollapalooza 1996

James Hetfield of Metallica wearing a silver choker necklace that matches his low-slung chain belt. Lollapalooza 1996

Tim Mosenfelder/Getty Images
Melissa Auf Der Maur performs during Lollapalooza.

Hole’s Melissa Auf Der Maur in a giraffe print top and copious amounts of jewelry. Lollapalooza 1995

Photo: Kevin Estrada / Media Punch
A little French chapeau on Luscious Jacksons Jill Cunniff. Lollapalooza 1994

A little French chapeau on Luscious Jackson’s Jill Cunniff. Lollapalooza 1994

Steve Eichner
Babes in Toylands Kat Bjelland showcases the “kinderwhore” look of the era in a vintage slip dress and baby barrettes....

Babes in Toyland’s Kat Bjelland showcases the “kinderwhore” look of the era in a vintage slip dress and baby barrettes. Lollapalooza 1993

Steve Eichner/Getty Images
A perfect look from Tools Maynard James Keenan. Lollapalooza 1997

A perfect look from Tool’s Maynard James Keenan. Lollapalooza 1997

Bob Berg/Getty Images
Jennifer Finch of the band L7 performs during Lollapalooza 1994

L7’s Jennifer Finch in a mask and a Spinal Tap shirt in front of a winter wonderland despite the fact this photo was taken in August in Philadelphia. Lollapalooza 1994

Photo: Lisa Lake/Getty Images
George Clinton of ParliamentFunkadelic during Lollapalooza 1994

Parliament-Funkadelic’s George Clinton…
 


Photo: Steve Eichner/Wire Image
…and DeWayne “Blackbyrd” McKnight who were never known for their minimalist approach to anything. Lollapalooza 1994

…and DeWayne “Blackbyrd” McKnight, who were never known for their minimalist approach to anything. Lollapalooza 1994

Tim Mosenfelder/Getty Images
Stereolabs Tim Dame and Laetitia Sadier in statement glasses and a delicately embellished shift dress respectively....

Stereolab’s Tim Dame and Laetitia Sadier in statement glasses and a delicately embellished shift dress, respectively. Lollapalooza 1994

Ebet Roberts/Getty Images
Holes Courtney Love in a vintage slip and the most important accessory for musicians of the decade a Built by Wendy...

Hole’s Courtney Love in a vintage slip and the most important accessory for musicians of the decade, a Built by Wendy guitar strap. Lollapalooza 1995

Photo: Kevin Mazur Archive 1/WireImage
When all else fails tightie whities do the trick just ask Flea of the Red Hot Chili Peppers. Lollapalooza 1992

When all else fails, tightie whities do the trick, just ask Flea of the Red Hot Chili Peppers. Lollapalooza 1992

Lisa Lake/Getty Images