Lizzy Gardiner (1995)
Gardiner, the Australian costume designer behind the 1994 film Priscilla: Queen of the Desert, made waves when she wore a dress made from American Express cards to the 1995 Academy Awards. While it's now a memorable red carpet moment, Gardiner told the ABC: "On the night it really upset a lot of people. A lot of women, I think they felt upstaged or pissed off that I wasn't taking things as seriously as I should."
Kate Moss (1993)
At an Elite Modelling Agency party in 1993, Kate Moss attended in what she had no idea was a sheer dress, and found out the hard way after stepping in front of flashing cameras.
"It was the first time I really got papped", the supermodel said in a 2017 interview. "I had no idea why everyone was so excited—in the darkness of [photographer Corinne Day]'s Soho flat the dress was not see-through!"
Princess Diana (1994)
On the same day that Prince Charles came clear about his affair with Camilla, Duchess of Cornwall (then Camilla Parker Bowles), Diana snatched the global headlines by wearing this royal 'revenge dress' by Greek designer Christina Stambolian. It's since become one of the most iconic dresses of all time, and marked Diana's newfound independence from the royal family.
Elizabeth Hurley (1994)
Hurley was a relatively unknown figure when she attended the Four Weddings And A Funeral premiere with her then-boyfriend, Hugh Grant, in this iconic safety-pin dress by Gianni Versace. The dress catapulted Hurley to global stardom, and proved that a single dress can be the ultimate branding choice.
Sarah Jessica Parker (1997)
SJP has had her fair share of controversial fashion moments, even before she was cast on Sex and the City. For the 1997 VH1/Vogue Fashion Awards, SJP wore this perilously backless pink mini, which looked like a regular slip dress from the front—a look reminiscent of Carrie Bradshaw's infamous 'naked dress'.
Cindy Crawford (1991)
Crawford, a bona fide supermodel, wore this red Versace gown to the Academy Awards in 1991 with her then-husband, Pretty Woman actor Richard Gere. The dress became famous for its low cleavage cut, which was rare (and very risqué) for its time.
Jada Pinkett-Smith (1997)
In the same year she married her husband, Will Smith, Jada Pinkett-Smith attended the 1997 Academy Awards in a stunning lamé two-piece ensemble, which showed her neon underwear underneath. In 2019, actress Zoë Kravitz wore her own version of the look to the Vanity Fair Oscars Party, instead with an Elsa Peretti-designed gold bra by Tiffany & Co.
Princess Diana (1996)
Diana attended the 1996 Met Gala in New York wearing a custom lingerie-style gown by John Galliano for Dior. The sleeveless, lacy gown was risqué for a royal family member—but Diana made it look as graceful as ever.
Rose McGowan (1999)
Charmed actress Rose McGowan attended the 1999 MTV VMAs with her then-husband, rock singer Marilyn Manson, and wore a completely sheer dress on the red carpet. While the front was revealing, the back was a whole different ballgame—covering McGowan's back with only a few thin strings.
In 1991, Madonna was the biggest star in the world, and sent waves when she cosplayed as Marilyn Monroe at that year's Academy Awards. Though Madonna was obviously channelling Monroe's style, the dress held an even closer connection to the late actress, as its designer, Bob Mackie, also designed Monroe's dress for when she sang 'Happy Birthday' to President John F. Kennedy in 1962.
Mariah Carey (1997)
In 1997, Carey had her own 'revenge dress' moment after a tricky split with her manager-turned-husband Tommy Mottola. At the 1997 VMAs, Carey wore this barely-there two-piece, which aided her transition to a more mature market.
Lil' Kim (1999)
In 1999, the 'How Many Licks?' rapper wore this lingerie set and sheer skirt to present an award to her friend, the late Alexander McQueen, at the VH1/Vogue Fashion Awards, seeing her transition from performer to fashion icon.
Salma Hayek (1997)
In red carpet history, there are a few thigh-high leg split moments that changed the game. One of the most famous was Salma Hayek's dress at the 1997 Met Gala, which left only a tiny piece of fabric between her upper and lower waist.
Celine Dion (1999)
Though it's not a dress, Dion's backwards Dior suit at the 1999 Academy Awards is considered one of her most memorable—and perfectly foreshadowed her modern-day style resurgence.
Demi Moore (1989)
Okay, we know it was slightly before the '90s, but Moore's unholy ball gown/bike shorts combo deserves an honorary mention. Considering the divisive modern infatuation with bike shorts, this dress could honestly be somewhat on-trend nowadays.