At Lilith Fair, Impeccable ’90s Style

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Photo: Fiona Apple, Ebet Robert/Redferns; Sarah McLachlan Erykah Badu, Tim Mosenfelder/Getty Images

A new documentary has been announced about Lilith Fair, the all-female music festival founded by the Canadian musician Sarah McLachlan in 1997. The film is reportedly based on the oral history that ran in Vanity Fair in 2019 (which you should definitely read). When the news broke early this month, it was huge news for both fans of female singer-songwriters everywhere and older millennials, like me, who came of age during this incredible time.

I never got to attend a Lilith Fair—I grew up in Puerto Rico, and the tour was strictly North America based—but for the three years it ran, it was like a distant dream. I had fallen in love with Sarah McLachlan’s record Surfacing on the strength of its first two singles, “Building a Mystery” and “Sweet Surrender,” which were on heavy rotation on VH1 at the time. So were Paula Cole’s “Where Have All the Cowboys Gone?,” Shawn Colvin’s “Sunny Came Home,” and all the hits from Sheryl Crow’s self-titled sophomore album and, of course, Fiona Apple’s debut, Tidal. It was a great time for women musicians and their fans, even if, at the time, they were still derided and all the main festivals of the era were increasingly macho in the worst possible way.

As the story goes, McLachlan was pissed that radio execs and concert promoters balked at the idea of playing two female artists back-to-back. So out of spite, she planned a whole music festival. She named it after Lilith, who was Adam’s wife before Eve and, according to Jewish folklore, was banished from paradise for refusing to be subservient to him.

In its first year, the festival grossed $16 million, making it the top-grossing festival of 1997—no small feat considering that Lollapalooza and the Warped Tour were still at their peak in those years. McLachlan also donated a percentage of the proceeds to charity. The 1997 lineup had McLachlan and Suzanne Vega playing every tour date and a rotating cast of powerhouses that included all the artists mentioned above, plus Tracy Chapman, the Indigo Girls, Jewel, Joan Osborne, Lisa Loeb, Juliana Hatfield, Susanna Hoffs, Dido, Pat Benatar, Jill Sobule, Beth Orton, Morcheeba, and K’s Choice. (A total of 69 artists that first year grew to more than 120 by the festival’s last year in 1999.)

As a teenager at the time, this music and moment were incredibly formative, so I thought I’d now take a walk down memory lane (a.k.a. Getty Images) and see what was captured during the three years that the festival took place, from 1997 to 1999. Not surprisingly, the vibes are impeccable, and my playlists have gotten a real good update lately. I can’t wait for the documentary to come out and perhaps inspire a new version of Lilith Fair for our modern era. In my dreams the lineup would include Charli XCX, Olivia Rodrigo, Chappell Roan, Solange, Lorde, St. Vincent, Kim Gordon, and Billie Eilish—yes, along with Sarah, Fiona, Erykah Badu, and of course Sheryl. Why not?! Dreaming is free.

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I have a feeling Sarah McLachlan was big into Dries Van Noten at the time.
Lilith Fair, 1998


Photo: Tim Mosenfelder/ImageDirect
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Erykah Badu’s vibes, impeccable as always.
Lilith Fair, 1997


Photo: Tim Mosenfelder/Getty Images
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If you look closely, you can see that Fiona Apple’s tank has an embroidered apple on the front.
Lilith Fair, 1997


Photo: Ebet Roberts/Redferns
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A live version of Sinead O’Connor’s “Fire on Babylon” can be found on the Lilith Fair compilation CDs released in 1999.
Lilith Fair, 1998


Photo: Steve Granitz/WireImage
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We all had hippie embroidered cotton blouses like Paula Cole’s in 1997.
Lilith Fair, 1997


Photo: Bob Berg/Getty Images
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Before the Indigo Girls became Barbie’s favorite band, they performed at Lilith Fair. Here, Amy Ray expertly mixed stripes on stripes…
Lilith Fair, 1998


Photo: Tim Mosenfelder/ImageDirect
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…while Emily Saliers kept it classic with a pair of overalls.
Lilith Fair, 1998


Photo: Tim Mosenfelder
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Natalie Merchant wore an incredible pleated wrap cardigan and flowers in her hair. Lilith Fair, 1998

Photo: Steve Granitz/Wire Image
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Many songs on Jewel’s hugely successful debut album, Pieces of You, were written when she was a teenager.
Lilith Fair, 1997


Photo: Bob Berg/Getty Images
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Liz Phair’s sporty platform sandals and long dress are as cool now as they were back then—just like her 1993 debut, Exile in Guyville.
Lilith Fair, 1998


Photo: Steve Eichner/Getty Images
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No one’s cooler than Missy Elliott.
Lilith Fair, 1998


Photo: Steve Eichner/Getty Images
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Sheryl Crow’s lacy top matched the intricate design of her bass.
Lilith Fair, 1999


Photo: Tim Mosenfelder/ImageDirect
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A better look at Sheryl Crow’s bass (and a perfect all-white outfit, to boot)
Lilith Fair, 1999


Photo: Debra L Rothenberg/FilmMagic
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Cibo Matto’s Yuka Honda and Miho Hatori performing with Sean Lennon
Lilith Fair, 1999


Photo: Tim Mosenfelder/Getty Images
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The Pretenders’ Chrissie Hynde matched her silver jacket to her silver guitar.
Lilith Fair, 1998


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Meshell Ndegeocello rocked a groovy denim-on-denim look.
Lilith Fair, 1998


Photo: Tim Mosenfelder/ImageDirect
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Beth Orton in a cowboy hat and tinted sunglasses is peak 1999 fashion. (For more peak 1999 vibes, check out her song “Stolen Car.”)
Lilith Fair, 1999


Photo: Tim Mosenfelder/Getty Images
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A million girls on Instagram would kill for Mya’s little floral wrap top and perfectly ripped jeans.
Lilith Fair, 1999


Photo: Tim Mosenfelder/Getty Images
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The Murmurs’ Heather Grody and Leisha Hailey performed in matching outfits.
Lilith Fair, 1999


Photo: Tim Mosenfelder/Getty Images
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Jill Cunniff of Luscious Jackson showed off her “Ladyfingers”…
Lilith Fair, 1999


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…and Vivian Trimble kept it cool in all black and tinted aviators.
Lilith Fair, 1999


Photo: Tim Mosenfelder/Getty Images
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Emmylou Harris performed at Lilith Fair in 1998 and 1999.
Lilith Fair, 1998


Photo: Bill Tompkins/Getty Images
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Before Lilith Fair the festival launched in full, Sarah McLachlan did a test run, playing a show with Suzanne Vega, above, along with Paula Cole and Tracy Chapman.
Lilith Fair, 1999


Photo: Debra L Rothenberg/FilmMagic
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Shawn Colvin rocked reflective sunglasses and a funky hat.
Lilith Fair, 1997


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Sixpence None the Richer’s Leigh Nash in a very ’90s combo of a tank top, so-called invisible beaded choker, and chunky gemstone ring.
Lilith Fair, 1999


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Billie Myers’s “Kiss the Rain” was a certified bop in the late ’90s.
Lilith Fair, 1998


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Yes! Sandra Bernhard performed at Lilith Fair.
Lilith Fair, 1999


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Closing out with another one of McLachlan because this bedazzled pants (Gucci?) and white tank combo is perfection.
Lilith Fair, 1999


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A close-up look at Badu’s makeup
Lilith Fair, 1998


Photo: Tim Mosenfelder/Getty Images