The 68 Most Iconic Fashion Moments in Grammy Award History

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Design by Morgan McMullen

The 2020 Grammy Awards will take place on January 26, 2020, and I personally can't wait to see what Cardi B, Lizzo, and Kacey Musgraves will be wearing. Obviously, it's all about the music, but it's also not just about the music—the Grammys are one place where artists always love to flex and express themselves through fashion. We've rounded up the most eye-catching, sparkly, and jaw-dropping outfits of the past 61 years and all I can say is...besides on your NYE dress, sequins belong at the Grammys.

<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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1 of 68
1974

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.

<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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2 of 68
1975

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

The 19th Annual GRAMMY Awards
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3 of 68
1977

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

<p>Pat Benatar wearing a stunning lace-up dress and purple eye makeup.&nbsp;</p>
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4 of 68
1982

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

<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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5 of 68
1983

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

<p>Cyndi Lauper keeping it quirky in a very '80s mash-up of colors and prints.&nbsp;</p>
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6 of 68
1984

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

<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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7 of 68
1986

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

<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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8 of 68
1988

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

<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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9 of 68
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.

34th Annual Grammy Awards
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10 of 68
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.

<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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11 of 68
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.

<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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12 of 68
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.

37th Annual Grammy Awards - Press Room
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13 of 68
1995

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

The 38th Annual GRAMMY Awards - Press Room
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14 of 68
1996

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

15 of 68
1997

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

Ron Galella Archive - File Photos 2011
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16 of 68
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.

<p>Li'l Kim wearing sheer tights and an equally sheer wrap over her bodysuit.&nbsp;</p>
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17 of 68
1998

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

<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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18 of 68
1999

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

<p>One of Madonna's most famous performances, wearing a Kabuki-like red frock to perform "Nothing Really Matters."</p>
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19 of 68
1999

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

<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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20 of 68
1999

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

<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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21 of 68
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.

<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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22 of 68
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.

<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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23 of 68
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.

24 of 68
2001

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

<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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25 of 68
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.

<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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26 of 68
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.)

27 of 68
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.

<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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28 of 68
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.

29 of 68
2004

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

<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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30 of 68
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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