The 25 Most Memorable Grammy Looks of All Time

7 minute read

While the Grammys recognize the best of the best in the music industry, the ceremony is also a huge night for fashion, a fact that’s not lost on style-savvy artists.

While some go for full-on glamour like J. Lo in her infamous green Versace dress in 2000, others have used red carpet fashion as yet another medium to express themselves. Case in point: Lady Gaga’s show-stopping ensembles that could function as performance art.

Throughout the years, there have been some especially unforgettable style moments at the Grammy ceremony — take a look at the most memorable looks of all time below.

Aretha Franklin, 1970

Aretha Franklin With Her Grammy Award
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Aretha Franklin picked up her Grammy in 1970 in a regal red and gold gown with a matching scarf.

Cher, 1974

Cher At The Grammys
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A young Cher showed off her famously toned abs at the 1974 Grammy Awards with a sheer white bandeau top and matching butterfly accessories.

Grace Jones and Rick James, 1983

The 25th Annual GRAMMY Awards - After Party at the Biltmore Hotel
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If there was ever a duo that embodied the gender-blurring, decadent funk of the ’80s, it would be none other than Rick James and Grace Jones who presented an award together in 1983. The supermodel singer wore a structurally ambitious dress and a sweeping hat, while James sported an embellished jacket, leather trousers and his trademark braids.

Michael Jackson, 1984

The 26th Annual GRAMMY Awards - After Party at Jimmy's
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The King of Pop glittered on the 1984 Grammys red carpet in an ensemble that included all the elements of his now-legendary style: aviator sunglasses, a bedazzled military-inspired jacket resplendent with epaulets and a sash, and of course, his iconic jeweled glove.

Cyndi Lauper, 1984

The 26th Annual GRAMMY Awards
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Cyndi Lauper’s eccentric fashion statement and coordinating eye makeup at the 1984 Grammy Awards proved that she was, indeed, “so unusual.”

Prince, 1988

30th Annual Grammy Awards
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—The Purple One took his already outrageous style to new heights with his ensemble for the 1988 Grammy Awards, where he wore a low cut, double-breasted, black-and-white polka dotted suit with a pair of matching high heels. The gender-fluid getup was a sign of the times. If there was anyone who had to match the over-the-top looks of the ’80s, it was definitely Prince.

Gwen Stefani, 1997

The 39th Annual GRAMMY Awards
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Stefani’s never been one to dress demurely, as evidenced by many of her late ’90s outfits. When she showed up to the Grammys in 1997, Stefani wore a slip dress and matching dress with chinoiserie vibes, accessorizing her look with her trademark red lip and a devil-may-care attitude. Stefani also sported a thoroughly un-P.C. bindi, something she’s been criticized for more than once.

Erykah Badu, 1999

41st Annual Grammy Awards - Arrivals
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The queen of neo-soul brought funky elegance to the Grammy Awards in 1999 with a leather patchwork column dress and a matching head wrap.

Lauryn Hill, 1999

The 41st Annual GRAMMY Awards
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Lauryn Hill opted for a casually chic look of a cropped sweater and a maxi skirt to pick up a record-setting five Grammys for her now-iconic The Miseducation of Lauryn Hill.

Jennifer Lopez, 2000

42nd Annual Grammy Awards - Pressroom
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Has there ever been another dress more memorable than J. Lo’s infamous down-to-there-slit-up-here green Versace dress that she wore to the 2000 Grammy Awards? Let’s put it this way: Google only let people search for text until this dress. Because of the record number of queries for Jenny’s provocative look, the search engine created a way for people to find images.

Britney Spears, 2000

The 42nd Annual GRAMMY Awards
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Spears’ Grammy debut had the pop princess trading in her girl-next-door appeal for some serious glam: her Oscar de la Renta dress paired with a fur stole and diamond jewelry showed that Brit could clean up nicely.

Destiny’s Child, 2001

43rd Annual Grammy Awards
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Destiny’s Child collected their Grammys in 2001 in looks by none other than the inimitable Tina Knowles, who created nearly all of their infamous matching outfits during their early years as a girl group.

Christina Aguilera, 2001

43rd Annual Grammy Awards
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This look was Aguilera at the peak of her “Xtina” phase; while there were no chaps on the red carpet for this event, Aguilera still commanded the red carpet by wearing a macrame-esque dress.

Toni Braxton, 2001

43rd Annual Grammy Awards - Pressroom
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Toni Braxton left little to the imagination when she wore a breezy dress to pick up her Grammy in 2001.

Lil’ Kim, 2002

The 44th Annual Grammy Awards
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Lil’ Kim took her signature racy style literally when she showed up on the Grammy red carpet in 2002 clad in a pair of low-slung, moto-inspired red leather pants and a matching cropped jacket. Rounding out her look? A Chanel belt and motorcycle helmet.

OutKast, 2002

The 44th Annual Grammy Awards
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OutKast looked spottieottiedopaliscious — that is to say, suavely dapper — in pastel colored suits and fly accessories (a fuzzy topper for Big Boi and Adidas superstars for Three Stacks) at the 2002 Grammys.

Avril Lavigne, 2003

The 45th Annual GRAMMY Awards - Arrivals by Jeff Kravitz
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ttLavigne channeled her skater girl persona with a punky ensemble that included Chuck Taylor high-top sneakers, a bow tie, and a blazer with a very important message in electrician’s tape.

Missy Elliott, 2003

The 45th Annual GRAMMY Awards - Arrivals
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Before the term “athleisure” was coined, Missy Elliot was rocking Adidas tracksuits with vim on the red carpet. Her pink velour one at the 2003 Grammy (where she collected an award for “Scream a.k.a. Itchin'”) paired with classic Adidas shell-toe Superstars, chain, and a fluffy hat was not only super duper fly, but a refreshing respite from the usual parade of gowns.

Tina Turner, 2008

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Tina Turner showed off the most iconic gams in the game when she wore a metallic leather jumpsuit while performing with Beyoncé in 2008.

M.I.A., 2009

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M.I.A. might have shared the Grammys stage with the most recognized names in hip hop in 2009 during a performance of T.I.’s “Swagga Like Us” — appearing with the likes of Jay Z, Lil Wayne, Kanye West, and Tip — but all eyes were on her as she rapped on stage in a sheer mini dress by House of Holland, while nine months pregnant.

Lady Gaga, 2010

52nd Annual GRAMMY Awards - Arrivals
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When Lady Gaga hit the Grammys’ red carpet in a structural, sparkling creation from Armani Privé in 2010, it was clear that the pop star was truly out of this world. While Gaga would show up to other shows in other outlandish looks (including, memorably, an egg at another Grammy ceremony and a meat dress at the MTV Video Music Awards,) this galactic dress set a precedent for the zany style that became Gaga’s default awards show attire.

Nicki Minaj, 2012

The 54th Annual GRAMMY Awards - Arrivals
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Nicki Minaj got tongues wagging when she showed up at the 2012 Grammy Awards dressed in a dramatic, bright red Versace cape and an unusual accessory — a plus one who was dressed like the Pope.

Pharrell, 2014

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Pharrell took home four Grammys in 2014 after having a landmark year. However, it was his tall, Arby’s-esque Vivienne Westwood topper that was the talk of the ceremony both on and off the red carpet, inspiring its own parody Twitter account. It later sold for over $40,000 to benefit his educational non-profit, From One Hand to AnOTHER.

Rihanna, 2015

57th GRAMMY Awards - Arrivals
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Rihanna’s rosy, voluminous Giambattista Valli couture gown wasn’t just show-stopping on the Grammy’s red carpet — the many layers of silk and tulle made the dress so large that it appeared to take up multiple seats and made Ri Ri visible from even the nosebleeds. In the true spirit of the Internet, the dress inspired comparisons to everything from a cupcake to a loofah.

Madonna, 2015

The 57th Annual GRAMMY Awards - Red Carpet
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While Madge has had her share of scene-stealing moments at the Grammy’s, her 2015 ensemble might have topped them all. Wearing a custom Givenchy look that looked part matador, part dominatrix, the Material Girl took the sexy look to the next level on the red carpets by flashing them, revealing a thong, fishnets, and her famously fit performer’s body.

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