POPSUGAR Fashion

The 50 Most Iconic Grammys Outfits of All Time

Jan 26 2014 - 3:25pm

The Grammy Awards are this Sunday, and this is one red carpet not to be missed. You just know that when the fashion and music industries come together, some very interesting things are bound to happen. Just in time for Throwback Thursday, we went back into the photo archives to bring you some of the most iconic fashion moments from the big show. Get ready for the gowns that stunned, shocked, and completely surprised us. And when you're done scrolling through these blasts from the past, be sure to check out POPSUGAR Beauty's best Grammys makeup mishaps [1] for some hilarious looks.

— Additional reporting by Robert Khederian

Iconic Grammys Style

What a trio: Brooke Shields [2], Michael Jackson [3], and Emmanuel Lewis hit the red carpet together in 1984.

Iconic Grammys Style

Adam Levine and Anne V upped the ante for sexiest red carpet couple in 2012.

Iconic Grammys Style

Beyoncé's short and sexy sequined number dazzled us in 2010.

Iconic Grammys Style

Katy Perry [4] surprised us all at the 2012 show, hitting the red carpet in a demure baby-blue Elie Saab [5] gown, which matched her aqua-colored hair to perfection.

Iconic Grammys Style

Willow Smith wore a kooky-cool outfit on the red carpet with dad Will in 2011.

Iconic Grammys Style

Katy Perry [6] (in a pair of angel wings, no less) hit the red carpet with then-husband Russell Brand [7] in 2011.

Iconic Grammys Style

M.I.A. showed off her baby bump in 2009.

Iconic Grammys Style

Yes, Fergie [8] was in a trio called Wild Orchid back in 1999, and yes, they wore these sequined dresses to the Grammys that year.

Iconic Grammys Style

Kanye West [9] channeled Prince's "Purple Rain" days for the 2006 show.

Iconic Grammys Style

Pink wasn't afraid to show some skin in this billowy white look back in 2002.

Iconic Grammys Style

Madonna [10] hit the stage in a red cape during the 1999 show.

Iconic Grammys Style

Solange Knowles posed with The Pussycat Dolls in 2008.

Iconic Grammys Style

Chaka Khan rocked a metallic purple taffeta ensemble back in 2005.

Iconic Grammys Style

Cher turned on the goth in 2008.

Iconic Grammys Style

Rihanna [11]'s barely there Jean Paul Gaultier [12] gown garnered a ton of attention in 2011.

Iconic Grammys Style

Kelly Rowland caught our attention on last year's red carpet in a Georges Chakra Couture, which showcased subtle flashes of skin and clung perfectly to her figure.

Iconic Grammys Style

Solange Knowles kept it short and poufy while big sis Beyoncé went all-out fancy in 2008.

Iconic Grammys Style

Mariah Carey [13] attended Jermaine Dupri's afterparty in a formfitting velvet gown in 2006.

Iconic Grammys Style

The ladies of Destiny's Child shone in a multitude of green lace and sequins in 2001.

Iconic Grammys Style

It couldn't have been easy to sit behind Lady Gaga [14] at the 2010 show — this futuristic costume was just one of several that evening.

Iconic Grammys Style

Kim Kardashian [15] looked like a Grammy statue herself in a low-cut gold Basil Soda gown in 2011.

Iconic Grammys Style

Jack Nicholson [16] and Diana Ross came undone in 1991.

Iconic Grammys Style

Rihanna [17] performed in this feathery frock during the 2008 show.

Iconic Grammys Style

Jennifer Lopez [18] flaunted a lot of leg and bared some shoulder in an asymmetrical Anthony Vaccarello gown in 2013. She carried a gold-plated clutch and finished off her ultrasexy ensemble with a pair of strappy heels.

Iconic Grammys Style

Lady Gaga [19]'s showstopping 2010 red carpet look was nothing short of fascinating.

Iconic Grammys Style

Katy Perry [20] went for the gold in 2010.

Iconic Grammys Style

The hair! The blazers! Supermodel Rachel Hunter attended the 1991 show with then-husband Rod Stewart.

Iconic Grammys Style

Britney Spears [21] and Alicia Keys [22] both got the pirate memo in 2002.

Iconic Grammys Style

Lil' Kim styled up sheer layers in 1998.

Iconic Grammys Style

Imogen Heap looked like a modern-day Mary Poppins in 2007.

Iconic Grammys Style

Nicki Minaj arrived in a statement-making red robe on the arm of a pope-like figure in 2012.

Iconic Grammys Style

Lady Gaga [23] hatched out of her incubating egg while opening the show in 2011.

Iconic Grammys Style

Michael and Janet Jackson [24] shared a sweet family moment (in matching black and white looks) in the Grammys press room in 1993.

Iconic Grammys Style

Beyoncé and Prince coordinated in shades of purple and pink for their Grammys performance in 2004.

Iconic Grammys Style

Rihanna [25] worked a bold and beautiful, fiery-red Alaïa gown at the 2013 awards.

Iconic Grammys Style

Last year, Beyoncé was a standout in a chic black and white jumpsuit by Osman Yousefzada [26].

Iconic Grammys Style

Estelle upped the ante on the red carpet in 2013 with a bold print on her cropped top and full-length skirt — a look she designed.

Iconic Grammys Style

We love Tina Turner's savage-chic look from 1982.

Iconic Grammys Style

Singing legend Diana Ross wore an eye-catching purple coat in 2006.

Iconic Grammys Style

Here's Cyndi Lauper doing her wild thing in 1984.

Iconic Grammys Style

Fergie [27] hit the red carpet in a bright orange lace Roberto Cavalli [28] gown at the 2012 show.

Iconic Grammys Style

Avril Lavigne [29] was feeling rebellious on the red carpet in 2003.

Iconic Grammys Style

Britney Spears [30] went for a glamorous all-white look in 2000.

Iconic Grammys Style

Naomi Campbell [31] wore a whimsical party-girl ensemble for the 1991 show.

Iconic Grammys Style

Just one of Lil' Kim's many over-the-top red carpet getups; the year was 2002.

Iconic Grammys Style

Nicki Minaj was covered in spots on the 2011 red carpet.

Iconic Grammys Style

Ashanti wore a peekaboo nude, embroidered look in 2005.

Iconic Grammys Style

Rihanna [32]'s custom-made Armani [33] gown sizzled on the red carpet in 2012.

Iconic Grammys Style

Grace Jones gave us a strong-shouldered spandex look in 1987.

Iconic Grammys Style

Faith Hill [34] wore a floral gown and curly hairstyle at the 1999 show.


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