Photo by Ron Galella/Ron Galella Collection via Getty Images, Barry King/Liaison, Jim Smeal/Ron Galella Collection via Getty Images

7 iconic 90s Oscars outfits

Love it or hate it, the awards show has given us some of the most iconic dresses of all time.

by Zoë Kendall
25 March 2022, 8:00am

Photo by Ron Galella/Ron Galella Collection via Getty Images, Barry King/Liaison, Jim Smeal/Ron Galella Collection via Getty Images

Love it or hate it, the Oscars are back to its regularly scheduled programming. This year, the ceremony will return to the Dolby Theatre and its usual late-February slot for the first time since the beginning of the pandemic. A celebration of all things cinema — visionary direction, evocative screenplays and tour-de-force performances — the annual ceremony is the film industry’s big night out. And vis-a-vis its famous red carpet, a big night for fashion, too. 

Since its inception, the Academy Awards have been the venue for some of history’s most iconic style moments. Of the 33 dresses with dedicated Wikipedia entries, 21 originally graced the ceremony’s red carpet. Over the years, Oscars style has had a massive impact on the fashion industry and its trend cycles. And in no decade is this seen more than the 90s. In 1991, Cindy Crawford’s red Versace launched a thousand knock-offs. Gwyneth Paltrow’s Ralph Lauren delighted; Lizzy Gardiner’s AmEx gown provoked. Some dresses shifted the zeitgeist, and some continue to influence, today. In anticipation of Sunday’s ceremony — and, of course, its red carpet — we’re looking back at the most iconic Oscars outfits from the 90s.

cindy crawford in a red versace dress posing on the oscars red carpet with richard gere 1991
Photo by Ron Galella/Ron Galella Collection via Getty Images

Cindy Crawford, 1991

In 1991, Cindy Crawford attended the Oscars as a plus-one — and outshone everyone officially invited. Accompanying then-boyfriend Richard Gere, the supermodel wore a plunging, firetruck-red gown designed by Versace. Not only did the dress steal the night, it influenced fashion trends into the early 90s, inspiring a slew of imitations and knock-offs for fans of the look. Since its turn on the red carpet, the dress has gone down in Oscars history, earning its own Wikipedia entry and a perennial place on the ceremony’s all-time lists. A testament to its reputation, the dress was auctioned for just over $12,500 in 1999.

geena davis posing on the oscars red carpet in a white dress 1992
Photo by Miranda Shen/Fotos International/Getty Images

Geena Davis, 1992

Geena Davis has always been one to turn an Oscars look. And in 1992 — the year she was nominated for Thelma & Louise — she pulled a show-stopper. If you think this Ruth Meyers look seems a little over-the-top (corset, ruffled train, tights and evening gloves?) then you’re spot on. Outlining her design notes to Time Magazine, Geena said, “I want to marry the Moulin Rouge to the Black and White Ball, and I want Christo and Jean-Claude to design the bridal gown and the wedding cake.” The campy confection landed Geena on the year’s worst-dressed lists, but, nonetheless, it ended up becoming one of the decade’s most memorable Oscars looks.

lizzy gardiner wearing a gold american express card dress on the oscarsred carpet 1995
Photo by Barry King/Liaison

Lizzy Gardiner, 1995

In 1995, Australian costume designer Lizzy Gardiner pulled up to the Oscars red carpet wearing one of her own designs: a column gown made of 254 expired American Express Gold Cards. The outré, Paco Rabanne-esque gown was originally conceived for comedy The Adventures of Priscilla, Queen of the Desert and was inspired by Sydney’s drag culture. The dress didn’t make it to the film’s final cut (AmEx forbade it), but Lizzy decided to pull it from her archives for the ceremony. While the look was skewered by critics (Time called it “tacky” and Cosmo dubbed it one of the “worst Oscar dresses of all time”), Lizzy had the last laugh: wearing her gold AmEx dress, she scooped the Best Costume award for the rest of her Priscilla garb.

nicole kidman posing on the oscars red carpet in a john galliano for dior couture dress 1997
Photo by Ke.Mazur/WireImage

Nicole Kidman, 1997

We love when a plus-one upstages her date — especially when it’s Nicole Kidman. In 1997, Nicole took to the Oscars red carpet in a gown that would change Oscars fashion forever. The dress in question was an elaborate and electrifying chartreuse gown, designed by Dior’s John Galliano. Compared to the award show’s typically tame garb, the eccentric look — with its fur trim and ornate embroidery — was a major fashion risk. But one that paid off. Red carpet correspondents dubbed the look as one of the award show’s “first true couture dresses.” Beyond the evening’s ceremony, the dress moved the needle of Oscars style towards the more experimental styles we know and love today.

jada pinkett smith in a versace set with will smith at the 1997 oscars
Photo by Jim Smeal/Ron Galella Collection via Getty Images

Jada Pinkett Smith, 1997

Long before the many chainmaillooks of Y2K, Jada Pinkett Smith was wearing Versace to the 1997 Oscars. The metal-mesh, midriff-bearing set was a daring departure from the award show’s typical ball gowns, but perfectly captured fashion’s zeitgeist — in 1997, Versace was the designer du jour. Without a doubt, this sexy, slinky look influenced the stylings of future stars, Y2K to 2020.

gwyneth paltrow holding her oscar in a pink gown 1999
Photo by Jim Smeal/Ron Galella Collection via Getty Images

Gwyneth Paltrow, 1999

At the 1999 Oscars, Gwyneth Paltrow made headlines not only for her Best Actress win, but for her dress: a pink taffeta Ralph Lauren ballgown,As Gwyneth told Vogue, the dress was made custom, just for her, after she’d requested a similar pink skirt from the designer’s seasonal lookbook. (“It was in the days before stylists,” she smiles.) At the time, the dress was polarizing among fashion critics and fans. Some praised its return to Old Hollywood glam. Others derided its bubblegum hue. Into the 21st century, however, the dress has consistently ranked as one of the Oscars most iconic dresses. It, too, even has its own Wikipedia page.

celine dion posing in a backless tuxedo on the oscars red carpet 1999
Photo by Jim Smeal/Ron Galella Collection via Getty Images

Céline Dion, 1999

This is the look that transformed Céline Dion from musical legend into the fashion icon she is today. In 1999, the singer took to the Oscars red carpet in a backwards Dior tuxedo (and fedora). In an era when red carpet womenswear was limited to evening gowns, Dion’s look was panned by fashion critics, who saw the look as too avant-garde. Of the risky ensemble, Céline told People, “I was the only one with pants in a backward suit from Galliano and if I would do this today it would work.” Céline was just way ahead of her time.

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