The 52 Most Iconic Fashion Moments in Grammy Award History

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

Yoko Oko and John Lennon are young and in love (and looking very sharp) at the '75 Grammy's.

Pat Benatar wearing a stunning lace-up dress and 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.

Michael Jackson wearing the sparkly sequined jacket of dreams (his signature white socks and black shoes not pictured).

Babs 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, from the custom high-waisted suit to the 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.

In case you ever doubted that Mariah Carey was the O.G. goddess of music events (let's just forget that New Year's Eve performance ever happened, okay?), refer to this vintage photo of her stunning in a scarlet gown.

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

Fiona Apple's silk cheongsam was a vastly different red carpet look from her peers, who chose floor-length gowns and glamorous get-ups.

Gwen Stefani also chose an Asian-inspired number for the event, but she opted for a silk jacket and a floor-length floral gown instead.

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

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

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

One of Madonna's most famous performances, wearing a Kabuki-like red frock to perform "Nothing Really Matters."

Britney Spears playing up va-va-voom Marilyn Monroe glamour in this all-white combination (almost as iconic as her Canadian tuxedo collaboration with Justin Timberlake at the American Music Awards).

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).

One of Christina Aguilera's most risk-taking red-carpet fashion moments wearing corn-rows and what looks like a sheer beach cover-up.

When your whole squad dresses up like Eve in the Garden of Eden.

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

The time brave soul Alicia Keys tried to make rainbow lashes and a sparkly hooded dress/jeans/tee combo a red carpet staple (we still love her though).

Gwen Stefani looks every bit the modern version of Jean Harlow (who 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's coordinated Converses with her entire crew.

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

That ideal, super relatable moment when your gold dress perfectly matches your many trophies.

Diana Ross wows in head-to-toe florals at Clive Davis' pre-Grammy Awards party.