The Most Daring Grammy Awards Fashion Looks of All Time

Jennifer Lopez, Lady Gaga, Nicki Minaj and Lil Kim are just some of the stars who have turned heads on the Grammy Awards red carpet with their eclectic looks.

By Corinne Heller Jan 21, 2020 11:00 AMTags

When it comes to daring fashion, can anyone top J.Lo this year at the 2020 Grammy Awards?

Jennifer Lopez famously wore a green plunging Versace gown to the 2000 ceremony, and it was even more risqué for its time. The singer and actress last year recreated the look, wearing an even sexier version of it—no really—at one of the designer's fashion shows and looked better than ever.

Lady GagaMadonnaCardi BNicki Minaj and Lil Kim are more stars who have turned heads on the Grammy Awards red carpet with their eclectic looks. While the stars are both known for her wild styles, and there was one year in particular where Gaga hatched up quite the fashion plan and entrance!

Gaga is expected to attend the 2020 Grammys, as she is nominated for three awards for her music in the hit remake A Star Is Born. Madonna is also nominated for an award, for Best Remixed Recording, and Cardi and husband Offset received a nod for their track "Clout."

Grammys 2020: Snubs and Surprises

Check out the most daring Grammy looks of all time:

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.

Demi Lovato

The "Confident" singer made a grand entrance at the 2017 event wearing an audacious gown by Julien Macdonald. From the plunging keyhole detail to the peek-a-boo material, this was one hot number.

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.

Destiny's Child

Destiny's Child lit up the red carpet in eye-catching ensembles at the 2001 event. They each wore glimmering green outfits that featured intricate beading and a unique ivy-like pattern.

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!

Christina Aguilera

The Grammy winner shined as bright as her trophy, as she dazzled in a silver chainmail dress by Versace. The pastel-colored butterflies, asymmetrical hemline and plunging neckline made it all the more memorable.

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.

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The 2020 Grammy Awards will air live from Staples Center in Los Angeles on CBS on Sunday, January 26 at 5 p.m. PT / 8 p.m. ET.

Check out a full list of Grammy nominations.