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Most Daring Grammy Awards Looks of All Time

38 photos
Jan 29, 2025 9:55 PM
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Blac Chyna, 2023 Grammys
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(Photo by Jeff Kravitz/FilmMagic)

Blac Chyna

Got pants? The reality star didn't with her 2023 Grammys look. Instead, she wore an extravagant, gothic-inspired black bodysuit adorned with feather plumes, intricate beading and a bejeweled hood. 


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Picture Perfect/Shutterstock

Katy Perry

Looking angelic! The pop star turned the 2011 event into her fantasyland, as she stunned in a frosted silver dress by Giorgio Armani. And the bustier's Swarovski crystals made the custom creation all the more heavenly.


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Ron Galella/Ron Galella Collection via Getty Images

Naomi Campbell

The supermodel stunned in a wildly colorful strapless dress that she styled with a lavish red feather boa at the 1991 ceremony.


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Dua Lipa

Dua Lipa's see-through Versace dress will surely make us nostalgic for Grammys fashion in the future!


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Jeff Vespa/WireImage

Nicki Minaj

The Queen rapper took pop culture fans to church in 2012. She traipsed down the red carpet wearing a crimson-colored design by Versace, which was adorned with the brand's famous logo in black sequins.


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Jon Kopaloff/Getty Images

Leon Bridges

A fashion statement—quite literally! The Texas native paid tribute to his home state with a custom-made Bode suit that featured delightful decals and fun drawings that referenced the Lone Star state.


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Madonna

Madonna made sure all eyes were on her in 2015. The star's Givenchy look certainly brought the theatrics with an excessively laced corset that she styled over an equally dramatic dress. Her veiled hat, fishnets and over-the-knee boots tied it all together.


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Rich Fury/Getty Images for The Recording Academy

Aterciopelados

Going for the gold! Aterciopelados' singer Andrea Echeverri pushed the fashion envelope wearing a trophy-inspired design at the 2019 show.


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Larry Busacca/Getty Images For The Recording Academy

Lady Gaga

The singer always knows how to make an entrance, however, this one took the cake. In 2011, she sent worldwide shock waves when she showed up—wait for it—inside an egg.


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Tammie Arroyo/Getty Images

Annie Lennox

The legendary singer turned the 1995 red carpet into a fashion fantasy as she donned a Minnie Mouse-inspired outfit—complete with the character's famous ears. However, the black leather dress and matching knee-high boots gave it an edge.


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Jordan Strauss/AP/Shutterstock

Phoebe Bridgers

Phoebe Bridgers didn't wait until Halloween to break out this skeleton look! The "Kyoto" singer graced the 2021 Grammys red carpet in a jacket and skirt decorated in crystal and pearl embellishments to look like bones.


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(Allen J. Schaben / Los Angeles Times via Getty Images)

Doja Cat

The "Woman" rapper is no stranger to a daring look on the red carpet. And this time around, for the 2024 ceremony, she credited her revealing sheer dress to designer Dilara Findikoglu with a Gothic-style temporary tattoo on her forehead. 


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Frazer Harrison/Getty Images

CeeLo Green

The singer and record producer left his classic tuxedo at home and, instead, opted for a metallic gold get-up that brought out his alter ego: Gnarly Davidson.


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Britney Spears

The "Lucky" singer oozed with glamour in a simple, yet striking slip dress that featured curve-hugging material and a plunging neckline. The decadent fluffy scarf added an extra touch of luxury.


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