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Lollapalooza Through the Years: 10 Iconic Moments In Style

From Devo to Sonic Youth, artists whose performances transcended music

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Crystal Castles demand your attention. The band's live performances convey a gleeful venom lacking in many of their contemporaries, thanks mainly to frontwoman's Alice Glass's fearless stage histrionics and savagely cool personal style.  It's all in the execution: her ink-black bowl haircut, Cheshire Cat sneer, and brutishly rendered eye makeup all scream "Fuck You," even when Glass's own glitched-out shrieks are incomprehensible. Ironically, Glass's nihilistic facade only makes people love her more; her look has been eagerly co-opted by dozens of American Apparel-clad  youths.

By Colleen Nika

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Sonic Youth (1995)

Though she never demands the spotlight, Kim Gordon's intuitive, artfully louche look  has become as crucial a motif to the fabric of alternative culture as Sonic Youth's music. It transcended grunge and became a founding cornerstone for future interpretations of "downtown cool" meant to a new generation of budding designers and stylists. The, same year her band auspiciously headlined 1995's Lollapalooza, she even helmed her own anti-fashion label, X-Girl. By the time the Youth played Lolla again in 2006, Gordon had become a front row fixture at New York designers like Marc Jacobs and Rodarte.

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Patti Smith (2006)

Patti Smith is a fashion icon to those who like their womenswear to veer towards the androgynous and cerebral. Countless designers have taken cues from the singer's "pagan poet" aura, especially Belgian maverick Ann Demeulemeester, who has composed several collections in tribute to the singer – they've even collaborated on multimedia projects together. In 2006, Smith played Lollapalooza in a signature genderless ensemble that incorporated a men's dinner jacket over a blouse – a hard/soft look beffitting the so-called godmother of punk, who can still blow the Docs off of anyone around her, regardless of gender or age.

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Karen O (2007)

Most of Karen O's on stage ensembles are hand-sewn creations made by friend, designer, and long-term collaborator Christian Joy. Often, they seem more like art installations than costumes, let alone clothing for mortals. Rumor is that an archive celebrating the most ambitious of these sartorial collaborations is in the works; if so, the look Karen sported for the Yeah Yeahs Yeahs' 2007 Lollapalooza performance will surely be noted as a high point. Dressed as a close approximation to a jester from outer space, the singer's look included a chevron-striped cape (that literally showered silver tinsel), a tutu mimicking a trash bag, and cage-printed tights. Just another day in the life of everyone's favorite punk art collagist.

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M.I.A. (2007)

M.I.A.'s eclectism encompasses every aspect of her artistic identity. Naturally, her brand of propulsive and vibrant polyglot pop demands equal audacity on the fashion front, which she certainly delivered during her bracing 2007 Lollapalooza performance. Outfitted in stridently printed booty shorts and a top seemingly composed a million lightning-bolt shaped puzzle pieces, her ensemble clashed as wondrously as her mutant beats, perfectly unifying her pioneering audiovisual manifesto. In a year where psychotic day-glo visuals ruled, M.I.A. was still the loudly clothed firebrand to beat.

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Hole (1995)

As Hole headlined 1995's Lollapalooza, frontwoman Courtney Love was reeling from a hellish year no one would let her forget. Bandmate tempers flared and clashed on a nearly nightly basis; violent backstage incidents between Love and other performers were common, as Kathleen Hanna will attest. But that summer, Love's stage attire drew as much attention as her behavior,  as she flaunted a more brazen version of her usual "kinderwhore" aesthetic. The singer's polarizing trifecta of wardrobe stables encompassed baby doll dresses (worn criminally short), smeared lipstick, and hooker heels – angry Lolita looks the catwalks of New York, Paris, and Milan were rampantly reproducing, as "heroin chic" officially became the defining aesthetic of the moody mid 90s.

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The Kills (2008)

The Kills perform at the 2008 Lollapalooza music festival at Grant Park on August 1, 2008 in Chicago, Without fail, any fashion editorial about about Alison Mosshart is required to contain the words "effortlessly cool." But at the risk of sounding trite, it's the most valid way to describe her enduring rock appeal. The Kills' frontwoman's charm is based in the luxury of not caring – a style philosophy espoused by one of her favorite designers, Rick Owens. For The Kills' performance at Lollapalooza 2008, Mosshart's uniform of choice was familiar to anyone who had seen one of the duo's electrifying live sets that year: a ratty leopard blouse worn over a torn Sass & Bide tee, drainpipe jeans, and well-worn Dior Homme gold boots. In the blistering August sun, her wild mane of black hair was tucked beneath a black sombrero, and Mosshart was drenched to the bone in sweat. She didn't care – and neither did her ecstatic fans.  In an epic case of woman vs. nature, Mosshart was clearly winning.

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The Jesus and Mary Chain (1992)

The Jesus and Mary Chain aren't innately fashionable, though William Reid arguably invented the most famous haircut in alternative rock history (whether he or Robert Smith inspired Johnny Depp's do in Edward Scissorhands can be endlessly debated.) But serendipitously paired with fellow shoegazers LUSH on the Lollapalooza '92 tour, JAMC ushered in a new colorful phase of their career, bolstered by trippier visuals – right down to their hair colors. That summer, William Reid's reinvention as a redhead matched Emma Anderson's own do rather harmoniously, lending an air of British eccentricity to the heavily American lineup.

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Nine Inch Nails (1991)

Not only did Trent Reznor and Co. bring a perverse fusion of industrial, nervy synth, and metal to the mainstream with breakout debut Pretty Hate Machine, their pivotal, set-destroying performance at 1991's Lollapalooza went on to be hailed one of the most iconic live milestones of the 120 Minutes era. Shrouded in gloom onstage, Reznor's morose, but entincingly groomed personal appearance elevated him to the status of a symbolic dark prince among kids preferring their iconoclasm a little less grungy.

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Devo (2010)

It wouldn't be Devo with a hooky visual gimmick, and last year, the new wave pioneers made a triumphant live return, culminating in a well-attended set at Lollapalooza. The comeback naturally entailed a dose of costume mischief – with a twist. This time, the band ditched their iconic red "energy domes" for their slightly-less-infamous yellow "radiation" suits, which the truly hardcore can actually purchase online, if they so desire.

In This Article: Lollapalooza, Lollapalooza 2011

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