20 of the Most Daring Fashions Ever Worn on the Red Carpet

20 of the Most Daring Fashions Ever Worn on the Red Carpet

When we think of “daring red carpet fashion” we no doubt are reminded of Jennifer Lopez’s envelope-pushing Versace dress from the 2000 Grammy Awards. However, there have been many red carpet moments both before and after JLo’s headline-grabbing slip of green fabric.

Some fashions left spectators scratching their heads, cracking up, or just plain wondering “How does she keep it on?” Here are 20 that you may or may not have seen for yourself.

1. Nicki Minaj at the 2012 Grammys

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Image Source: eonline.com

Back when Nicki Minaj was still cementing herself in the public consciousness, she took some very Gaga-esque fashion risks, including this unholy look. Nothing gets people talking quite like sacrilege.

2. Cher at the 1988 Academy Awards

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Image Source: chernews

When you see the parade of nudity on display at every single awards show happening today, remember that all of these women owe trailblazer Cher a lot. The primary difference is that she managed to do it while accepting an Oscar.

3. Toni Braxton at the 2001 Grammys

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Image Source: dailymail.co.uk

You have to hand it to Toni – a lot of starlets will go for slits that high, but many don’t consider these handy hip straps to hold what’s left of the dress halfway in place. This look made more headlines than her actual win.

4. Julia Roberts at the 1999 Premiere of Notting Hill

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Image Source: eonline.com

Back in 1999, actress Julia Roberts hit the red carpet for her movie Notting Hill happy and ready to smile and wave for cameras and fans. Her personal choice to not shave her underarms was considered very shocking, proving that the dress isn’t everything.

5. Rihanna at the 2014 CFDA Awards

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Image Source: ohnotheydidnt

It’s Rihanna’s world, and you just live here. She wore this custom Adam Selman ensemble to pick up a Style Icon award, and later lamented that her only regret in life was not wearing a bedazzled thong to cap it off.

6. Lil Kim at the 1999 MTV VMAs

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Image Source: dazeddigital.com

A lot of Americans didn’t know exactly what pasties were until Lil Kim wore one, resplendent in purple and silver sequins, to the VMAs. More shocking was the moment Diana Ross gave her exposed breast a little lift, as though she was shaking her hand.

7. Bjork at the 2001 Academy Awards

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Bjork’s swan dress was mocked mercilessly for an entire year after she wore it, but as usual, the musician was way ahead of her time. It has since gone on display at the Metropolitan Museum of Modern Art.

8. Celine Dion at the 1999 Academy Awards

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Image Source: people.com

Celine Dion also believes she was ahead of her time when she wore this backwards tuxedo by Galliano in 1999. It got poor reviews back then, but she’s probably right – fashion critics are much more forgiving about suits these days. John Galliano, on the other hand, has fallen from most people’s good graces.

9. Beyoncé at the 2015 Met Ball

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Image Source: popsugar.com

Beyoncé’s sheer Givenchy was the highlight of the Met the night she took to the red carpet late to debut it. Given that there were similar nude illusion looks on the scene that night, we have to wonder if she just wanted to have the final word.

10. Geena Davis at the 1992 Academy Awards

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Image Source: oscar.go.com

This very odd creation has stuck in people’s minds as one of the most questionable red carpet fashion choices of all time. Geena is known for her brains and talent, but the gloves, the train, the bubble skirt – it never ceases to befuddle.

11. Miley Cyrus at the 2015 MTV VMAs

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Image Source: zimbio.com

The rebellion of Miley Cyrus may have been an artistic choice meant to separate her from the pack, and this suspenders-and-chain-mail getup is certainly one way to get the message across. Where else was she going to wear those boots?

12. Bella Hadid at the 2017 Cannes amFAR Gala

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Image Source: zimbio.com

When you’re best known for wearing clothes, you can’t miss a single event without making a fashion statement. The trouble is, model Bella hasn’t quite nailed the fine art of wearing very little without flashing the goods – she’s had numerous wardrobe malfunctions.

13. Margaret Cho at the 2004 Grammys

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Image Source: eonline.com

Known more for her humor than her fashion choices, Margaret Cho shocked audiences when she appeared on the 2004 Grammys red carpet in full-on peacock plumage. How many birds were sacrificed for this getup?

14. Rose McGowan at the 1998 MTV VMAs

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Image Source: huffingtonpost.com

Behold one of the very few images of Rose at the 1998 VMAs that’s not completely NSFW. She later stated that this dress was a political statement, and that she wanted to wear something really rebellious. At the time, it truly was.

15. Gwyneth Paltrow at the 2002 Academy Awards

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Image Source: huffingtonpost.com

For those who think you can’t go wrong with an Alexander McQueen, take a good look at Paltrow in 2002. The ruched bust, the unfortunate gathering at the hips – it wasn’t anyone’s proudest moment, and was about eight years too late to pass as grunge.

16. Lady Gaga at the 2010 MTV VMAs

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Image Source: hollywoodreporter.com

You knew we were getting around to this. Lady Gaga has waxed intellectual many times about why she chose to wear raw meat to the VMAs, but the bottom line is that no one loves a dress that looks only half as bad as it probably smells.

17. Jennifer Lawrence at the 2017 Premiere of Mother!

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Image Source: people.com

You may not prefer barely-there gowns because they lack elegance and artistry, but then there’s Jennifer Lawrence in this Atelier Versace number at a London film premiere. The intricate web of beadwork is show stopping.

18. Britney Spears at the 2001 American Music Awards

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Image Source: style.nine.com.au

Nothing reminds us of early 2000’s fashion quite the way the phrase “patchwork denim” does. Spears brought it to the red carpet, complete with date Justin Timberlake in a denim cowboy hat. Photos are forever, kids.

19. Katy Perry at the 2014 MTV VMAs

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Image Source: instyle.co.uk

If you’re ever preparing for a red carpet appearance, and don’t know how to get your lion’s share of attention, just rip a page out of someone else’s playbook. Perry did when she recreated Britney’s denim gown, solidifying its transition from dated to iconic.

20. Jennifer Lopez at the 2015 Met Ball

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Image Source: instyle.com

The Met theme of “Through the Looking Glass” meant “You can see through my dress” for many stars that year. Lopez, always sure to make waves with a red carpet look, wore a dragon made from jewels and little else.

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