The 50 Most Iconic Grammy Awards Red Carpet Looks

Leave it to Grace Jones to bring avant garde fashion onto the Grammy scene. The singer shut down the red carpet for the award show’s 25th anniversary in an ultra wide-brim hat (which Rick James posed under) and matching black leather ensemble.

Donna Summer gave us the leopard x Southern belle mashup we didn’t know we needed with this animal print hoop skirt featuring tulle underlay.

One of MJ’s most iconic looks, the King of Pop showed up to the ’84 Grammy Awards in a bedazzled military jacket and what would become his signature single glove.

Always one to push gender norms in fashion, Prince wore a polka-dot suit with matching high heeled boots to the 1988 Grammys.

En Vogue showed up to the 1991 Grammy Awards in traditional African looks that brought some much-welcomed color and print to the red carpet that year.

Gracing the music award show with her presence, Naomi Campbell delivered a major ’90s fashion moment in a colorful mini dress and red feather boa.

In one of the Grammys’ first-ever naked dresses, Celine Dion showed up to the 1993 show in a see-through black lace gown that showed off her black thong.

That same year, Janet Jackson and Michael Jackson had a matching sibling moment in chic white suits and red ribbons to raise awareness for AIDS.

Bow down to the legendary head-to-toe leopard look Mary J. Blige graced everyone with at the 38th annual Grammy Awards. She even rocked black sunglasses and leather gloves inside the show like a boss.

An iconic fashion moment in girl band history, TLC wore matching white silky outfits for their first-ever Grammy appearance where they swept the awards with four wins.

One of Lauryn Hill’s most underrated Grammy looks, the singer stunned in a red-and-white dress, toe-ring sandals, and a matching red choker.

In one of the most stunning red-carpet maternity dresses of all time, Jada Pinkett Smith wore a sheer sparkling gown to the 1998 Grammys.

Lil’ Kim brought on the shine factor with glitter tights, a sparkling cardigan, and bejeweled heels.

Wearing a Nefertiti headwrap and leather patchwork gown, Erykah Badu’s effortlessly cool look at the 1999 Grammys was unforgettable.

Faith Hill’s ultra-feminine lilac gown and matching shawl looked straight out of a ’90s rom-com.

The dress that literally created Google Images, Jennifer Lopez’s plunging Versace gown is one of the most impactful red carpet looks of all time. At the time, the belly-button baring look was one of the most scandalous gowns to grace a red carpet and it remains one of the most iconic to this day.