Fashion
What Mariah, Billie & More Wore To Win Best New Artist At The Grammys
Four stars wore the same designer.
The 2025 Grammys are a few days away, and in the spirit of retrospection, we’re taking another trip down memory lane to see what the Best New Artist award recipients wore the night they won. Many people in the industry think the award is a “curse,” and while that may be true for acts like Milli Vanilli, the seemingly unwanted award has been an accurate predictor of the superstars of tomorrow, with recent winners like Billie Eilish, Dua Lipa, and Megan Thee Stallion.
Getting dressed for such a big night is now a full-fledged event, and many of the outfits below weren’t even the red-carpet looks stars wore to start the night, but rather the second (or third) ‘fit they slipped into to take to the stage and pick up the award. With an incredibly stacked nominee pool this year including Chappell Roan, Sabrina Carpenter, and Doechii, we’re sure the winner will earn a spot in our best-dressed roundup and join the ranks of Mariah Carey and Christina Aguilera as a well-dressed newcomer. Keep scrolling to see the Best New Artist winners from Cyndi Lauper to Victoria Monét.
Cyndi Lauper, 1985
Don’t question why Hulk Hogan is in this picture, instead just appreciate her robe dress and crystal anklet.
Mariah Carey, 1991
A LBD to end all LBDs, perfectly accessorized by both drop earrings and two awards.
Toni Braxton, 1994
Ms. Braxton won in 1994, and dressed like a winner in this lacy red confection, paired oh-so well with her signature pixie cut.
Sheryl Crow, 1995
Bohemian dressing at the Grammys? It’s more likely than you think.
LeAnn Rimes, 1997
One of the ‘90s most successful artists kept this award in the country-sphere and chose a simple (and very ‘90s) slip dress and pendant necklace to win.
Lauryn Hill, 1999
This tulle skirt of many colors was counteracted by her simple black cropped T-shirt and megawatt smile.
Christina Aguilera, 2000
We previously featured this butterfly Versace dress in our roundup of the Grammys red carpet 25 years ago, and this look has staying power today.
Shelby Lynne, 2001
Bet you haven’t seen a velvet sky-blue two-piece hit the Grammys red carpet like this before. Bonus points for her tousled hair and midi boots.
Alicia Keys, 2002
This was Keys’ second look of the night, and this boho-goth mashup was a custom rework of an Alexander McQueen Spring 2002 runway look.
Norah Jones, 2003
A lesson in not doing too much, and wearing a comfortable heel height to hold up your multiple awards without breaking a sweat.
Evanescence, 2004
The goth princess of punk-rock posed solo with her band’s two awards in an emo Harajuku-inspired dress by Japanese designer h.naoto.
Amy Winehouse, 2008
Everyone can remember this instantly infamous moment, where Amy won five of six Grammys she was up for this year from across the pond at a concert in London. In true Amy style, she wore her hair and heels to the sky and a simple black slip dress.
Adele, 2009
The now 16-time Grammy winner won her first two gramaphones in 2009, wearing a custom Barbara Tfank hourglass dress and some timeless Manolo Blahnik buckle shoes.
fun., 2013
A very 2010s ultraskinny suiting moment (ankles must be exposed) from the band that, unfortunately, fell victim to the Best New Artist curse and have been on hiatus since 2015.
Sam Smith, 2015
A great lesson in male award-ceremony dressing.
Meghan Trainor, 2016
Made ya look! The singer went in red hair and a custom Michael Costello dress to win the award after just one album and hit song.
Alessia Cara, 2018
Another sign of the times look. The hoops and suit give Sade, but the Converse make it Tumblr kid.
Dua Lipa, 2019
Versace at the Grammys is always a good idea. Just ask Dua, who’s worn Versace a few times to the ceremony and wore this spliced dress to win two awards (and perform the sexiest duet with St. Vincent).
Billie Eilish, 2020
She won six awards that night, and wore three different Gucci outfits, including a blue and red tracksuit to the afterparty. But this black and gold set with a green turtleneck underneath.
Megan Thee Stallion, 2021
Miss “Savage” wore this orange dress with a massive bustle and train in back to win a Grammy with Beyoncé.
Olivia Rodrigo, 2022
Another Versace-clad Best New Artist, and the start of Rodrigo’s now-signature silhouette.
Samara Joy, 2023
The jazz singer ran away with a surprise win in this red-hot long-sleeve dress.
Victoria Monét, 2024
The most recent recipient marks the fourth time a winner’s worn Versace, officially cementing the Italian brand as a must-have when nominated.
