The 68 Most Iconic Fashion Moments in Grammy Award History

Cher arrived looking like the fairytale embodiment of Lisa Frank (in the best way possible) and setting the stage for the body-baring getups of future decades.

Yoko Oko and John Lennon are young and in love at the '75 Grammys.

My name is Bette Midler and I can wear a crown if I want to.

Pat Benatar wearing a stunning lace-up dress and perfectly '80s purple eye makeup.

Rick James and a barely recognizable Olivia Newton-John dressed like they're each other's Grammy's prom dates. (Corsage not included.)

Cyndi Lauper keeping it quirky in a very '80s mash-up of colors and prints.

Barbra Streisand wearing gold lamé to accept an award for the Best Pop Vocal Performance for a Broadway Album.

Prince slaying in head-to-toe polka dots, including custom high-waisted suit and pointed heels.

Naomi Campbell strutting into the Grammy Awards wearing a mini dress inspired by a deck-of-cards and a fluffy red boa on top.

Where do we begin with a 1992 Celine Dion? The mules are fabulous, and so is this dress with tights—a rarity on the red carpet.

In case you ever doubted that Mariah Carey was the O.G. goddess of music events, refer to this vintage photo of her in a stunning scarlet gown.

Selena, the picture of red-carpet glamour, arrived at the Grammy's wearing a sparkly white halter dress, a bouffant, and her signature red lip.

Faith Hill looking like a vision in white with a plunging slit. Would totally wear this dress today.

Mary J. Blige in head-to-toe leopard print, black gloves, and sunglasses inside? Icon.

Gwen Stefani opted for a silk jacket and a floor-length floral gown.

Not sure who's more of a mood: a pregnant Jada Pinkett Smith in this very sheer, sparkly dress, or the guy behind her.

Lil' Kim wearing sheer (sparkly) tights and an equally sheer (sparkly) wrap over her bodysuit.

Faith Hill looking like a'90s princess (the same year Gwyneth Paltrow wore that powder-pink dress at the Oscars).

Madonna wearing a Kabuki-like red frock to perform "Nothing Really Matters."

J.Lo wore a dazzling sparkly gold mini dress, which was a pre-cursor to her big fashion moment ahead (see: 2000).

Arguably the most iconic Grammy's dress of all time (of all time!), J.Lo wore a pluuunging, sheer Versace dress and lots of double-sided tape...probably.

Britney Spears going for va-va-voom Marilyn Monroe glamour in this all-white combination. It's almost as iconic as her Canadian tuxedo collaboration with Justin Timberlake at the American Music Awards.

One of Christina Aguilera's riskiest and most controversial red-carpet fashion moments came in 2001 when she wore cornrows and what looks like a sheer beach cover-up.

Destiny's Child channeling Eve in the Garden of Eden.

Never one to wear anything close to boring, Lil' Kim rolled up to the red carpet in leather pants, a bikini top, and matching red shades. #Hero.

That one time brave soul Alicia Keys tried to make rainbow lashes and a sparkly hooded dress/jeans/tee combo work. (We still love her, though.)

Gwen Stefani looks every bit of a modern version of Jean Harlow (whom she played in 2004's The Aviator) in a skin-baring white getup and white-blonde pin curls.

Avril Lavigne giving the middle finger to gender norms in a full-on suit (top hat not pictured), but like, the Hot Topic version. Note that she has coordinated Converses with her entire crew.

Alicia Keys looking stunning in a two-tone peach gown.