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