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Most DARING Grammys Fashion: JLo, Harry Styles, Madonna, Cardi B & More
Get ready to adore these pitch-perfect looks.
After all, when it comes to the Grammy Awards, celebs like Harry Styles, Sabrina Carpenter and Miley Cyrus know how to show out on the red carpet.
For the One Direction alum—whose first new album in four years is set for release in March—the biggest night in music has been the perfect place to show off his most eccentric looks.
For instance, Harry turned the 2023 red carpet into a rainbow paradise with his multi-colored Egonlab jumpsuit featuring a glittering diamond pattern. And when the "Aperture" singer took the stage, he emerged in a silver jumpsuit adorned with hundreds of shimmering fringes.
This year's award show at the Crypto.com Arena in Los Angeles will be an evening to remember, and not just because Harry is returning to the ceremony as a presenter. With Sabrina nominated in six categories at the Feb. 1 show, including Record of the Year and Best Pop Vocal Album, she is sure to dazzle on the red carpet.
In fact, the “Manchild” singer proved she’s always had good taste when she stepped out at the 2025 Grammys in a daring powder blue JW Anderson backless dress featuring a pear-cut diamond pendant cascading down her back and an ostrich feather trim along the hem and hips.
Among the most daring looks came from Chappell Roan, whose 2003 Jean Paul Gautier spring/summer couture collection gown was worthy of any art museum. In fact, the blue-and-yellow look was literally imprinted with Edgar Degas' portrait of ballerinas on the skirt.
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The "Pink Pony Club" singer—who is nominated for Record of the Year and Best Pop Solo Performance this year—completed her look with a feathered headpiece featured in the original runway show. Chappell's stylist Genesis Webb felt it was essential to have her client in archival couture.
"Regardless of the designer, I wanted something with history; something that carried weight beyond aesthetics,” she told Vogue last February. "Gaultier had been on my mind for her for some time, so I reached out, and when this particular archival piece was presented, I had an immediate visceral reaction. It wasn't just an option, it was the dress. While I had several looks prepared for the fitting, this was the only one that truly aligned with the vision."
As the curtain slowly begins to rise on the 2026 Grammys, keep reading for more celebs who didn't need any luck, babe, when it came to red carpet fashion.
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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.
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Rihanna
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.
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Cher
The legendary star basically invented daring fashion, and this white-hot number from the 1974 Grammys further cemented her status as a risk-taker.
(Photo by Gilbert Flores/Billboard via Getty Images)
Chappell Roan
The "Good Luck, Babe" singer channeled her hit song's cover art with a pig-nose and red Renaissance-era inspired dress at Universal's 2024 Grammy Awards after-party.
Frazer Harrison/Getty Images for The Recording Academy
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.
Kevin Mazur/Getty Images for The Recording Academy
Noah Cyrus
The Best New Artist nominee made a sartorial splash at the 2021 Grammys in this larger-than-life couture design by Schiaparelli.
Kevin Mazur/Getty Images for The Recording Academy
Doja Cat
Dare to bare! The "Say So" rapper took the plunge in a very low-cut Roberto Cavalli gown at the 2021 Grammys.
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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.
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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.
(Photo by Axelle/Bauer-Griffin/FilmMagic)
Harry Styles
The "Adore You" signer turned the 2023 Grammys red carpet into a rainbow paradise with a colorful sequined jumpsuit. And, of course, the butterfly tattoo had to make an appearance as well.
Kevin Mazur/Getty Images for The Recording Academy
Jasmine Sanders
Florals for spring? Well, Jasmine Sanders certainly made it groundbreaking with her sheer lace gown by Jean Louis Sabaji.
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Toni Braxton
The Grammy winner proved a dress can be regal and risquè all at the same time.
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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.
Lester Cohen/Getty Images for The Recording Academy
Spice
The Grammy nominee rivaled the red carpet in a larger-than-life ruffled robe that she paired over a plunging diamond-embellished dress.
(Photo by Lester Cohen/Getty Images for The Recording Academy)
Machine Gun Kelly
In case his silver-foil Dolce & Gabbana suit wasn't fabulous enough, MGK took his 2023 Grammys look to the next level with a glimmering crystal harness.
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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.
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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.
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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.
(Photo by Gilbert Flores/Billboard via Getty Images)
Miley Cyrus
The Disney alum dabbled with some heavy metals, stepping onto the 2024 red carpet in a custom Maison Margiela gold metal mesh dress. And, of course, she paired it with matching metal panties.
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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.
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TLC
The girl group proved sportswear could be just a chic and stylish as evening wear.
Frazer Harrison/Getty Images for The Recording Academy
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.
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Beyoncé
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.
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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.
(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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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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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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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.
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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