The 50 Most Iconic Fashion Moments in Grammy Award History

From the over-the-top to the drop-dead-gorgeous.

Perhaps the frocks are fancier at other award shows, but the Grammy Awards has never provided a shortage of outlandish and memorable fashion moments. Leave it to the musicians and presenters to parade the kookiest finery on music's biggest night of year. With 2017's Grammys right around the corner, we found it appropriate to take a stroll down memory lane and relive the most badass, beautiful, and bare-it-all moments of years past.

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1974

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. 

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1975

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

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1982

Pat Benatar wearing a stunning lace-up dress and purple eye makeup. 

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1983

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

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1984

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

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1984

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

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1986

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

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1988

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

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1991

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

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1993

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. 

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1994

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. 

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1997

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

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1997

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. 

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1998

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

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1999

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

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1999

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

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1999

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

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2000

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). 

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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). 

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2001

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

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2001

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

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2002

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

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2002

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). 

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2003

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. 

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2003

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. 

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2004

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

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2004

The dream team of Beyoncé  and Prince in one room performing "Purple Rain" and "Crazy in Love" was a spectacle not just for the musical collaboration.

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2004

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

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2005

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

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2006

Kanye, still in his aggressive sunglasses and white gloves phase, put the stuffy tuxedo in its place with this lilac number (note: with the sleeves rolled up). 

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