POPSUGAR Celebrity

The 50 Most Iconic Grammys Outfits of All Time

Feb 15 2016 - 4:00am

The Grammy Awards red carpet is one you don't want to miss. You just know that when the fashion and music industries come together, some very interesting things are bound to happen. 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.



Rihanna [5] worked a bold and beautiful, fiery-red Alaïa gown at the 2013 awards.

Britney Spears

Britney Spears [6] went for a glamorous all-white look in 2000.

Taylor Swift

Taylor Swift [7] went with a gorgeous J. Mendel gown in 2013.

Jennifer Lopez

Jennifer Lopez [8] wore that iconic Versace dress to the 2000 show.

Gwyneth Paltrow

Gwyneth Paltrow [9] sparkled in Versace in 2009.

Kim Kardashian

Kim Kardashian [10] wore Jean Paul Gaultier Couture to the 2015 awards.

Mariah Carey

Mariah Carey [11] went for a two-piece ensemble in 1996.

Katy Perry

Katy Perry [12] surprised us all at the 2012 show, hitting the red carpet in a demure baby-blue Elie Saab gown, which matched her aqua-colored hair to perfection.


Who didn't adore Adele's Valentino dress in 2015?

Beyoncé Knowles

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

Carrie Underwood

Carrie Underwood [13] went with long-sleeves back in 2012 wearing Gomez-Gracia.

Gwen Stefani

In 2006, a pregnant Gwen Stefani [14] wore L.A.M.B. to the Grammy Awards.


Rihanna [15]'s Giambattista Valli gown stole the show in 2015.


Rihanna [16]'s barely there Jean Paul Gaultier gown garnered a ton of attention in 2011.


In 2010, Ciara stunned in Givenchy.

Beyoncé Knowles

Beyoncé was a standout in a chic black and white jumpsuit by Osman Yousefzada in 2013.


Fergie [17] hit the red carpet in a bright orange lace Roberto Cavalli gown at the 2012 show.

Faith Hill

Faith Hill [18] wore J. Mendel in 2013.

Jennifer Lopez

Jennifer Lopez [19] flaunted a lot of leg and bared some shoulder in an asymmetrical Anthony Vaccarello gown in 2013.

Kelly Rowland

Kelly Rowland attended in a Georges Chakra Couture back in 2013.

Miley Cyrus

Miley Cyrus [20] wore Alexandre Vauthier in 2015.

Jennifer Hudson

Jennifer Hudson [21] wore a black peplum Victoria Beckham [22] number in 2010.

Alicia Keys

Alicia Keys [23] looked like a princess at the 2004 show.

Jack Nicholson and Diana Ross

Jack Nicholson [24] and Diana Ross attended in 1991.

Gwen Stefani

Gwen Stefani [25] wore a Versace jumpsuit to the Grammy Awards in 2015.

Fiona Apple

Singer Fiona Apple wore J. Mendel to the 2006 show.

Kim Kardashian

Kim Kardashian [26] looked like a Grammy statue herself in a low-cut gold Basil Soda gown in 2011.

Adam Levine and Anne V

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

Naomi Campbell

Naomi Campbell [27] wore a whimsical party-girl ensemble for the 1991 show.

Lady Gaga

It couldn't have been easy to sit behind Lady Gaga [28] at the 2010 show — this futuristic costume was just one of several that evening.

Diana Ross

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

Michael and Janet Jackson

Michael and Janet Jackson [29] shared a sweet family moment (in matching black and white looks) in the Grammys press room in 1993.

Rod Stewart and Rachel Hunter

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

Beyoncé Knowles and Prince

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

Katy Perry and Russell Brand

Katy Perry [30] (in a pair of angel wings, no less) hit the red carpet with then-husband Russell Brand [31] in 2011.

Lil' Kim

Lil' Kim styled up sheer layers in 1998.

Lady Gaga

Lady Gaga [32]'s showstopping 2010 red carpet look was nothing short of fascinating.

Nicki Minaj

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

Lady Gaga

Lady Gaga [33] hatched out of her incubating egg while opening the show in 2011.


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.

Tina Turner

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

Cyndi Lauper

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

Avril Lavigne

Avril Lavigne [34] was feeling rebellious on the red carpet in 2003.

Lil' Kim

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

Nicki Minaj

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

Grace Jones

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

Kanye West

Kanye West [35] channeled Prince's "Purple Rain" days for the 2006 show.

Britney Spears and Alicia Keys

Britney Spears [36] and Alicia Keys [37] both got the pirate memo in 2002.

Imogen Heap

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

Faith Hill

iFaith Hill wore a floral gown and curly hairstyle at the 1999 show.

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