The 1990s were a time of interesting (and often iconic) style, as well as a new attitude towards celebrity. More and more, we cared about the lives and outfits of the famous people we saw in Us Weekly and People, and wearing a daring dress might be enough to launch you into stardom or infamy (or both). It was also a time to be experimental and individual with fashion—including for events that were historically buttoned-up, like the Oscars—and we had red carpet outfits ranging from torn jeans and old boots to the most gorgeous low-cut Versace dresses. We had looks that caused quite a stir at the time but actually deserve a recalculation in 2023, as well as looks that might not have seemed as iconic as they do now.
Some of these looks you’re going to be familiar with (hello, Lil’ Kim, in your very daring purple ensemble!), and some of them you might not (ever heard of Lizzy Gardiner? Just wait), but keep scrolling, because the best red carpet looks of the ’90s are a truly wild trip down memory lane.
Drew Barrymore at ‘Guilty by Suspicion’ Premiere,’ 1991
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With a perfect cute/grunge red carpet aesthetic (often with a cigarette in hand), Drew Barrymore was the casual queen of ’90s events. This is the perfect iteration: matte lip, cream cardi, ripped jeans, worn brown boots.
Kate Moss and Christy Turlington, CFDA Awards, 1993
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The two ascending top models brought casual-chic style to the CFDAs with what would become the iconic look of the ’90s: minis and short jackets. Moss, who was a Calvin Klein muse, became particularly synonymous with the simple sensuality of the decade’s fashions.
Julia Roberts and Kiefer Sutherland, the Oscars, 1990
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Remember when Julia Roberts and Kiefer Sutherland dated? Also remember when they showed up to the Oscars with the same hairdo? In case you’ve forgotten, the then it-couple got engaged later that year and then suddenly broke it off—followed by a love triangle featuring Sutherland’s good friend Jason Patric.
Lizzy Gardiner, the Oscars, 1995
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Long before Lady Gaga even thought about her meat dress, Gardiner, a costume designer, went to the literal Oscars wearing hundreds of legit, expired Amex cards. Apparently it was an old (unused) costume. At the time, critics hated it, but it helped inspire creative red carpet fashion.
Angelina Jolie, screening of ‘Gia,’ 1998
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Jolie did all-black, modern, goth styling way before it was cool (and she can absolutely be credited with bringing the style to the red carpet). Back in the day, pairing your black sparkly dress with a knee-length black leather trench was incredibly surprising. This portrayal of the tragic Gia Carangi cemented her as both a talented actor and fashion force.
Kim Basinger, the Oscars, 1990
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Kim Basinger actually designed this wedding-esque gown herself, and critics…mostly hated it, to be honest. It was like a wedding gown merged with a smart white suit, but in hindsight (hindsuit?) it’s actually a pretty fun moment.
Whoopi Goldberg, the Oscars, 1993
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While most people at the time used the Oscars to break out their most formal couture gowns, Goldberg opted for a Wizard-of-Oz-esque pantsuit and green and purple cape. She was apparently “inspired” by Disney, and it was deemed a fashion fail at the time (and memorable today).
Fran Drescher, Golden Globes, 1996
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Considered an “unsung hero” of the ’90s Golden Globes, Fran Drescher went full Nanny with a simple, low-cut white dress and then just a full bouquet of flowers on her head. She was by now an eye-catching fashionista, so this was just the look to outdo herself.
Mariah Carey, 1997 MTV Video Music Awards
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Just after announcing her separation from husband Tommy Mottola and deciding to reinvent herself, Mariah Carey donned this epic outfit that felt like some pretty amazing revenge dressing. Carey was leaning into a new sound, and this accompanying new look was a hit with fans.
Jennifer Lopez, Limelight Club ‘Notorious’ Magazine Party, 1999
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J. Lo‘s been a style icon for a long time, but this look was one of the first. She was at an event with and being styled by Donatella Versace, who have had a long friendship. This would be only a year before J. Lo would don that green Versace, with the low front slit to her naval.
Cher, the Oscars, 1998
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Not quite the black spiky dress she donned in the ’80s, Cher nevertheless turned heads in this white Bob Mackie number that featured sheer details. She had long been known as “the person who dresses in the wildest Oscar outfits,” but fun fact: She hated this dress, but just never told the designer.
Celine Dion, the Oscars, 1999
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Lots of people have at least a vague recollection of this Dior suit—mainly because Celine Dion chose to wear the blazer backwards and don a fedora. People haaaated it at the time, but it actually gave us an intriguing backless shape that was a taste of Dion’s fun fashion choices to come.
TLC, Nickelodeon’s 12th Annual Kids Choice Awards, 1999
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TLC did fun matching outfits way before other “girl groups” did, but this graphic, color-blocked set of outfits for the Nickelodeon Kid’s Choice Awards might be the most notable—it’s known as one of the cutest coordinated looks the awards show has ever seen.
Kurt Cobain, Courtney Love, Frances Bean Cobain, MTV Video Music Awards, 1993
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In a grunge-focused awards ceremony, the late Kurt Cobain made a rare red carpet appearance with wife Courtney Love. The two posed as a family with daughter Frances Bean, with Cobain sporting a bottle as an accessory.
