Jennifer Lopez, Lady Gaga and More of the Most Daring Grammy Awards Looks of All Time

When it comes to the Grammys, most stars pride themselves in serving looks that are nothing less than fabulous.

After all, the glamorous music awards ceremony presents the perfect opportunity for celebs like Jennifer Lopez, Beyoncé and Billie Eilish to experiment with the most stunning and lavish ensembles that push the boundaries of fashion.

From her first Grammys outing in 2000, style icons like Britney Spears put in the work to emulate the very definition of chic. Indeed, the “Toxic” singer was the epitome of Y2K fashion at the early aughts ceremony, wearing a white slip dress with a plunging neckline with a white fur stole from Oscar de la Renta over top.

And as time went on, it seemed that wardrobe choices became even more extravagant and out of this world. While Lady Gaga pushed boundaries in 2010 with her galactic Armani Privé dress, she outdid herself the following year with an entrance that was simply unprecedented. Instead of walking the red carpet, the “Poker Face” singer was carried inside a gigantic egg before emerging in an all-yellow outfit.

Even in recent years, artists like Chappell Roan embraced the limitless bounds of curating the perfect outfit. And for the “Good Luck, Babe” singer, accessories played a key role. Recreating her hit song’s cover art at the 2024 Universal after-party, she wore a pig nose to complement her red Renaissance-era inspired red dress and velvet headpiece.

Beyond making waves in the world of fashion, let’s not forget the tangible and historic impact that J. Lo’s infamous 2000 Grammys Versace dress had on the world as we know it. The sheer green gown turned enough heads that Google had no choice but to quell worldwide curiosities by inventing a new feature: Google Image Search.

Ahead of the upcoming 2025 Grammys, held at the Crypto.com Arena on Feb. 6, scroll on to see some of the most audacious fashion moments in the music award show’s 66-year history…

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.

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 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.

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

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

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.

 

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.

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. 

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

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

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.

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.

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.

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.

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.

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 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.

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.

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.

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. 

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.

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

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

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.

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.