See the Most Daring Grammy Awards Looks of All Time

From Jennifer Lopez' iconic Versace dress to Lady Gaga's egg-cellent entrance, here are all the most jaw-dropping looks to have ever graced the Grammys red carpet.

By Gabrielle Chung Mar 31, 2022 1:00 PMTags
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When you're invited to music's biggest night, you have to turn up your fashion game.

While a little black dress is always a safe choice for the Grammys, stars like Lady Gaga, Billie EilishNicki Minaj and Madonna have taken things to the next level by using the ceremony's red carpet as an opportunity to show off their eclectic styles. We've seen some pretty daring drips over the years, whether it be celebs arriving in an egg-shaped pod or rocking head-to-toe florals (complete with a bucket hat and matching protective face mask per COVID-19 protocols, of course). 

After all, who can forget that Versace dress Jennifer Lopez wore to the 2000 Grammys? The low-plunging, see-through number caught so much attention at the time that it led to the creation of Google Image Search. In fact, the iconic gown even has its own Wikipedia page now.

In honor of the upcoming 2022 Grammys, held at the MGM Grand Garden Arena in Las Vegas on April 3, we're taking a look back at the most audacious fashion moments in the music award show's 64-year history.

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Scroll on to see all the head-turning ensembles that now live rent-free in our minds!

Jennifer Lopez

Green with envy! J.Lo shut down the red carpet at the 2000 Grammys in a daring green Versace design. The fashion moment was so iconic that Google Image Search was born.


The Fenty Beauty founder looked like a vision in white at the 2011 Grammys. She turned heads in a sheer off-the-shoulder dress by Jean Paul Gaultier.


The legendary star basically invented daring fashion, and this white-hot number from the 1974 Grammys further cemented her status as a risk-taker.

Lil Nas X

Lil Nas X made the red carpet his runway in a bright and bold pink Versace suit. From the daring harness to the gold-studded details, this was an outfit to remember.

Noah Cyrus

The Best New Artist nominee made a sartorial splash at the 2021 Grammys in this larger-than-life couture design by Schiaparelli. 

Doja Cat

Dare to bare! The "Say So" rapper took the plunge in a very low-cut Roberto Cavalli gown at the 2021 Grammys.

Lady Gaga

Galactic glam vibes. The pop star is known for her over-the-top getups and she didn't disappoint at the 2010 event when she showed up in a futuristic Armani Privé dress.


Cardi B

The "WAP" rapper made a tremendous splash at the 2019 ceremony with her vintage Thierry Mugler creation, which featured an oyster-like shell and dazzling pearl embellishments. Inspired by Sandro Botticelli's "The Birth of Venus," this look was a work of art.

Jasmine Sanders

Florals for spring? Well, Jasmine Sanders certainly made it groundbreaking with her sheer lace gown by Jean Louis Sabaji.

Toni Braxton

The Grammy winner proved a dress can be regal and risquè all at the same time.

Paula Abdul

All that glitters is gold. Paula Abdul brought the glitz and the glamour to the 1990 ceremony with her dazzling gold fringe dress.


The Grammy nominee rivaled the red carpet in a larger-than-life ruffled robe that she paired over a plunging diamond-embellished dress.

Billie Eilish

You should see her in a crown—or rather, a patterned suit complete with its own matching bucket hat and protective face mask as part of COVID-19 protocols.

Billy Porter

The Pose star stole the show at the 2020 Grammys in a glitzy teal jumpsuit that was embellished with diamond fringe. However, the motorized hat really took things to the next level.

Jada Pinkett Smith

The Red Table Talk host's nude-colored dress turned heads with its risquè cut-outs and body-hugging material. The knee-high strappy sandals added extra oomph.

Sheryl Crow

Sheryl Crow was nominated for "The First Cut Is the Deepest" at the 2005 Grammys—and she played it up by serving bawdy and face in a bright yellow gown with an exposed midriff and thigh-high slit.


The girl group proved sportswear could be just a chic and stylish as evening wear.

Tyler, the Creator

Inn-credible! The rapper donned an electrifying pink bellhop suit that he accessorized with a matching suitcase. And naturally, the clothes he would wear later that evening were tucked inside his luggage.


Queen Bey showed up and showed out wearing a majestic purple get-up. From the dazzling embellishments to the sheer material, the singer stunned from head-to-toe.

Lil' Kim

The Grammy-winning rapper set the red carpet in flames with her vermilion-colored ensemble. The star's Chanel motorcycle helmet and jewel-encrusted belt brought the wow factor.

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.

Naomi Campbell

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

Dua Lipa

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

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.

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.


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.


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

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.

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.

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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For a full recap of the 2024 Grammy Awards, visit E! Online's Grammys page for every photo, winner and OMG moment.