The 65 Most Iconic Fashion Moments in Grammy Award History

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Design by Morgan McMullen

Leave it to the musicians and presenters at the Grammy Awards to wear the craziest, most over-the-top outfits to celebrate music's biggest night of year. With the 2019 Grammy's 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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<p>Cher looking like the fairy-tale&nbsp;embodiment of Lisa Frank (in the best way possible),&nbsp;setting&nbsp;the stage for the&nbsp;body-baring&nbsp;getups of future decades.&nbsp;</p>
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1974

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

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<p>Yoko Oko&nbsp;and John Lennon are young and in&nbsp;love (and looking very sharp) at the '75 Grammy's.&nbsp;</p>
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1975

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

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The 19th Annual GRAMMY Awards
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1977

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

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<p>Pat Benatar wearing a stunning lace-up dress and purple eye makeup.&nbsp;</p>
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1982

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

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<p>Rick James and a barely recognizable Olivia Newton-John dressed like they're each other's Grammy's prom dates&nbsp;(corsage not included).&nbsp;</p>
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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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<p>Cyndi Lauper keeping it quirky in a very '80s mash-up of colors and prints.&nbsp;</p>
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1984

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

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<p>Babs wearing gold lamé&nbsp;<span class="redactor-invisible-space" data-verified="redactor" data-redactor-tag="span" data-redactor-class="redactor-invisible-space"></span> to accept an award for the Best Pop Vocal Performance for a Broadway Album.&nbsp;</p>
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1986

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

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<p>Prince slaying in&nbsp;head-to-toe polka dots, from the custom high-waisted&nbsp;suit to the pointed&nbsp;heels.&nbsp;</p>
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1988

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

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<p>Naomi Campbell strutting into the Grammy Awards wearing a mini dress inspired by a&nbsp;deck-of-cards&nbsp;and a fluffy red boa on top.&nbsp;</p>
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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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34th Annual Grammy Awards
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1992

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.

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<p>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&nbsp;this vintage photo of her stunning in a scarlet gown.&nbsp;</p>
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1993

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.

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<p>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.&nbsp;</p>
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1994

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.

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37th Annual Grammy Awards - Press Room
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1995

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

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The 38th Annual GRAMMY Awards - Press Room
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1996

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

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1997

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

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Ron Galella Archive - File Photos 2011
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1998

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

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<p>Li'l Kim wearing sheer tights and an equally sheer wrap over her bodysuit.&nbsp;</p>
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1998

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

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<p>Faith Hill looking like a'90s princess (the same year&nbsp;Gwyneth Paltrow made the powder-pink dress her domain at the Oscars).&nbsp;</p>
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1999

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

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<p>One of Madonna's most famous performances, wearing a Kabuki-like red frock to perform "Nothing Really Matters."</p>
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1999

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

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<p>J.Lo wore a dazzling sparkly gold mini dress, a pre-cursor to her big fashion moment ahead (see 2000).&nbsp;</p>
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1999

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

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<p>Arguably the most iconic Grammy's dress of all time (of all time!), J.Lo wore a <a href="http://www.marieclaire.com/celebrity/news/g4355/plunging-necklines-trend-golden-globes-2017/" target="_blank" data-tracking-id="recirc-text-link">pluuunging</a>, sheer Versace dress (and&nbsp;lots of double-sided tape, probably).&nbsp;</p>
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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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<p>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).&nbsp;</p>
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2000

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.

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<p>One of&nbsp;Christina Aguilera's most risk-taking red-carpet&nbsp;fashion moments wearing corn-rows and what looks like a sheer beach cover-up.&nbsp;</p>
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2001

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.

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2001

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

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<p>Never one to wear anything close to boring, this year&nbsp;Li'l Kim rolled up to the red carpet in leather hot pants, a bikini top, and matching red shades #hero.&nbsp;</p>
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2002

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.

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<p>The time brave soul&nbsp;Alicia Keys tried to make rainbow lashes and a sparkly hooded dress/jeans/tee combo a red carpet staple (we still love her&nbsp;though).&nbsp;</p>
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2002

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.)

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2003

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.

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<p>Avril Lavigne giving the middle finger to gender norms in a full-on suit (top hat not pictured), but like, the Hot Topic&nbsp;version. Note that she's coordinated Converses with her entire crew.&nbsp;</p>
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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 has 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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<p>The dream team of Beyoncé&nbsp;<span class="redactor-invisible-space" data-verified="redactor" data-redactor-tag="span" data-redactor-class="redactor-invisible-space"></span> and Prince in one room performing "Purple Rain" and "Crazy in Love" was a spectacle not just for the musical collaboration.</p>
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2004

Dream team Beyoncé and Prince performing "Purple Rain" and "Crazy in Love" was a spectacle...and not just for the musical collaboration.

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<p>That ideal, super relatable&nbsp;moment when your gold dress perfectly matches your many trophies.&nbsp;</p>
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2004

That super relatable moment when your gold dress perfectly matches your four trophies.

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<p>Diana Ross wows in head-to-toe florals at Clive Davis' pre-Grammy Awards party.&nbsp;</p>
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2005

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

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The 47th Annual GRAMMY Awards - Arrivals
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2005

Nobody rocks a fedora better than Penélope Cruz on the 2005 red carpet.

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<p>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).&nbsp;</p>
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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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The 49th Annual GRAMMY Awards - Arrivals
Jon KopaloffGetty Images
2007

Pictured: Isabella Hilary Duff in this amazing sequined slip dress. Paolo, where you at?

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<p>The year Kanye made those glow-in-the-dark&nbsp;shutter shades a thing (R.I.P.)&nbsp;</p>
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2008

The year Kanye made those glow-in-the-dark shutter shades a thing. R.I.P.

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<p>A very pregnant M.I.A. arrived at the awards show showing off her baby pump in this crazy but fabulous&nbsp;sheer polka-dot outfit.&nbsp;</p>
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2009

A very pregnant M.I.A. arrived at the awards show in this crazy-but-fabulous sheer polka-dot outfit that drew attention straight to her bump.

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