20 of the most daring looks of the '90s

Davis, who was nominated for best actress that year for her role in "Thelma and Louise,"wore a frothy gown designed by costume designers Ruth Meyers and Bill Hargate, but it was met with mixed reactions.

"The very campy confection landed the actress on that year's worst-dressed lists," journalist Jessica Winter wrote for Time in 2013. "Nonetheless, the get-up ended up becoming one of the decade's most memorable Oscars looks."

Goldberg's look — a brocade jumpsuit paired with matching shoes and a purple cape that she opened to reveal lime-green lining — was nothing short of daring. "After all, it is Hollywood," Goldberg said, The New York Times reported at the time.

In 2012, The Guardian named the eye-catching get-up one of the "10 most notorious frocks on the red carpet." "Sadly it tanked," journalist Morwenna Ferrier wrote.

At the premiere of "Four Weddings and a Funeral," which starred her boyfriend Hugh Grant, the model wore a black dress with a plunging neckline and a side slit held together by oversized gold safety pins.

The look did more than turn heads. According to Oscar Holland at CNN, Hurley "sparked a revolution in red-carpet eveningwear" and "thrust[ed] her out of Grant's shadow and into the international spotlight," he wrote in 2020.

Gardiner, known for her work on "Priscilla: Queen of the Desert," showed up to the 1995 Academy Awards in a dress made entirely of American Express cards. 

Decades later, in 2017, Gardiner told 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."

Twain rocked an all-black transparent look that exposed her undergarments at the 1996 Grammy Awards. 

Twain's daring fashion choices have carried over to the 21st century. In February, people compared her 2023 Grammys look — a black-and-white Harris Reed outfit with flared pants, a matching blazer, and top hat — to Cruella De Vil, and in April some music fans criticized her CMT Music Awards outfit choices: a semi-sheer butterfly-print gown and a sparkling crop-top-and-shorts set.

She responded to the critics via Instagram, where she posted a photo of the outfits, writing, "For me fashion is a powerful tool that helps to convey my personality and express my creativity."

"Other than getting to hang out with my friends for the night, [fashion is] one of my favourite things about attending award shows! Life is too short to wear boring clothes!!" she wrote.

In just one of many daring looks from her decades-long Hollywood career, Bullock walked the red carpet in a black lacy mini dress at the 1996 People's Choice Awards.

Taking a popular trend and making it her own, Mary J. Blige showed up to the 1996 Grammys in a full-body leopard suit that included a hood. The artist is known for her bold outfits.

This Versace set made a lasting impression on audiences, according to Fashionista, which put this look in its "Great Outfits in Fashion History" series.

Dion wore a see-through, crocheted gown to the Grammy Awards in 1997, where she won the award for album of the year for "Falling into You."

The actress wore a long-sleeved, see-through dress to the Vogue Fashion Awards in 1996. According to Wonderwall, she paired the dress with a velvet jacket which she took off for photos.

Audiences were shocked to see an almost-naked Rose McGowan on the red carpet at the 1998 VMAs.

"I did that for a reason," McGowan told Jameela Jamil in a 2019 interview. "It was my first public appearance after being raped."

One of the first women to claim to The New York Times and The New Yorker that she had been sexually assaulted by Harvey Weinstein, McGowan told Yahoo Entertainment in 2020 that although she's questioned her choice to wear the revealing outfit, ultimately, "I completely understand why I did what I did."

Now serving a 39-year-sentence for sexually assaulting multiple women, Weinstein "unequivocally denied" her allegations in 2017, according to his spokesperson.

McGowan's decision to wear the dress didn't come without backlash.

"It was kind of hard," she told Yahoo. "I hadn't really ever dealt with global media shaming. But it prepared me for later on it happening to me a whole bunch."

Parker wore this entirely backless DKNY slip dress to the Vogue Fashion Awards in 1997.

Many "Sex and the City" fans noted a similarity between her look and the "naked dress" that Parker wore on the show as her character, Carrie Bradshaw.

The front and back sides of Electra's black dress were held together by chains, in a look reminiscent of Elizabeth Hurley's safety-pin dress. This daring look was named one of the most risqué red-carpet looks of all time by British Vogue.

The rapper wore a bedazzled bikini with an equally shimmery headpiece and skirt on stage at the 1997 VMAs.

At the 1998 Oscars, Cher wore a shimmery, ultra-revealing Bob Mackie dress.

Cher defended her various risky looks in a 2013 interview with The Hollywood Reporter.

"I mean, I thought we were in show business," she said. "People can say I dressed like a fool, I don't have good taste. It's not about good or bad clothes; it's about freedom."

"People in our business do things that are out of the ordinary, so why seek approval? God knows every one of them has enough money to wear what they want!" she continued.

Paltrow wore a see-through Giorgio Armani gown covered in beads to the premiere of "Shakespeare in Love," in which she played the female lead.

Despite its modest length and neckline, the dress' transparency made it a daring choice.

Anderson paired a bustier top with a fluffy pink hat designed by Ivy Supersonic. In 2022, People referred to the look as "one of the most iconic red carpet looks" and a "favorite among fans and A-listers alike."

The look was especially daring, as it contrasted starkly with that of her date, Tommy Lee, who wore a Burberry trench coat.

In 1999, the rapper wore an elevated lingerie set to the Vogue Fashion Awards, where she presented Alexander McQueen with the award for fashion designer of the year.

The jumpsuit exposed one of Lil' Kim's breasts, which was covered by a seashell-shaped pastie. The look was described as one of the most "era-defining fashion moments of the '90s" by PopSugar.

In 2020, her stylist, Misa Hylton, told PopSugar, "I wanted to make something really ornate and feminine and pretty, to offset the fact that she had one breast out."

What might have been more daring than the look itself was Diana Ross' decision to touch the rapper's breast on stage on live TV.

She utilized the outfit's feathers to make a revealing top slightly more modest.