The 16 Craziest Grammy Outfits Since 2000

While the Grammy Awards are largely remembered for the performances and the curse of the best new artist category, you can also count on the annual event for some of the wackier red carpet outfits of awards season.

Here are 19 of the craziest looks from Grammys past, ranging from “OMG this is so crazy I need to have it in my closet” to “wow this person is crazy for thinking that was okay.”

1. Katy Perry, 2011

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Remember when Katy Perry was still married to Russell Brand and waltzed into the 2011 Grammy Awards looking like a Victoria’s Secret Model who got hit with a last minute sense of modesty? Yes, she’s wearing wings.

2. Kanye West, 2006

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Way before The Life Of Pablo came into our lives, Kanye showed up to the 2006 Grammys looking like a pimp who may or may not have just watched Prince’s “Purple Rain” on an endless loop for the past week.

3. Britney Spears and Alicia Keys, 2002

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Did they plan to both dress like pirate wenches, or was that just a big look this year?

4. Nicki Minaj, 2012

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Because nothing says ‘look at me bitches’ like showing up to the red carpet dressed as Little Red Riding Hood gone Versace, with a fake pope as your date.

5. Rihanna, 2015

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Hate it or love it, Rihanna’s pink princess Giambattista Valli gown turned every head in the room.

6. Jennifer Lopez, 2000

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The dress so iconic we don’t need to say anything else.

7. Pharrell Williams

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The hat that launched 1,000 memes.

8. Toni Braxton, 2001

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When you got it, flaunt it, girl.

9. Lil Kim, 2002

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Definitive proof that the early 2000s don’t have to make a fashion comeback. They just don’t.

10. Madonna, 2014

Everyone’s favorite pop queen went for the classic “slutty matador in the front, sluttier matador in the back” look.

11. Lady Gaga, 2011

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Remember that time Lady Gaga showed up to the Grammys inside of an egg?

12. Christina Aguliera, 2001

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Believe it or not, this isn’t even the weirdest hair decision Xtina made in her prime. It’s not even in the top 3.

13. Beyonce, 2004

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It’s hard to believe that there was a time when Beyonce style wasn’t flawless, isn’t it? This has to be a Tina Knowles special.

14. Lady Gaga, 2010

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Fabulous, but also super WTF.

15. Destiny’s Child, 2001

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Seriously, when is this reunion tour happening already?

16. Cee Lo Green, 2011

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We weren’t ready for this outfit in 2011, and we’re not ready for it now.


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