50 Most Memorable Grammy Looks

Suits, skulls and spandex: From J.Lo to John Lennon, see the night's most iconic fashion turns

01 of 50

SHEER EXPOSURE

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Talk about a showstopper! In 2000, Jennifer Lopez turned heads in this infamous sheer, cut-to-there Versace dress. Of the hoopla that ensued, Lopez, who attended with then-boyfriend Diddy, told Harper’s Bazaar, “Those fashion moments happen by mistake – you can’t plan things like that.”

02 of 50

HUNG UP

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Frank Micelotta/Getty

Opening the show in 2006, Madonna got physical in a lavender leotard and matching corset that showed off her yoga-toned body. Her performance was later banned from the Malaysian broadcast, after officials deemed her dance and costume too provocative.

03 of 50

THE MATCH GAME

THE MATCH GAME
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Long before Destiny’s Child, it was TLC’s Rozonda “Chilli” Thomas, Lisa “Left Eye” Lopes and Tionne “T-Boz” Watkins that made dressing alike Crazy Sexy Cool in 1996. “The Grammys are the most prestigious music event, and white is the richest color,” their stylist said. Ironically, the trio was battling back from bankruptcy at the time.

04 of 50

THE GREEN PARTY

THE GREEN PARTY

In 2001, Destiny’s Child – Kelly Rowland, Beyoncé and Michelle Williams – glittered in green ensembles designed by Beyoncé’s mother, Tina Knowles. Tina has since parlayed her love of design into a clothing line, House of Deréon, which she runs with daughters Beyoncé and Solange.

05 of 50

FITS LIKE A GLOVE

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WireImage

Setting off a massive trend, Michael Jackson wore just one bedazzled glove to the 1984 Grammys. It was a big night for Jackson and Grammy history – the self-proclaimed King of Pop took home a record-breaking eight awards.

06 of 50

BASIC BLACK

BASIC BLACK

With her naturally curly hair loose, in 1991, best new artist Mariah Carey was a “Vision” in a form-fitting little black dress. That year, she picked up her first two Grammys, receiving three more in 2005.

07 of 50

ANIMAL INSTINCT

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Celebrating the success of her first solo album, nominee and “Hollaback Girl” Gwen Stefani – who was pregnant with son Kingston – took a walk on the wild side in 2006. She’ll be sporting maternity wear this year again, as Stefani is expecting her second child.

08 of 50

AMAZING GRACE

AMAZING GRACE
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In 1983, Grace Jones – forever a fashion standout – kept hitting her co-presenter Rick James onstage with her unwieldy, futuristic ensemble. “I’ve always been a rebel,” the model and singer has said. “I never do things the way they’re supposed to be done.”

09 of 50

WHAT A GIRL WORE

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Jeffrey Mayer/WireImage

Nominee Christina Aguilera took a plunge in 2001 in this bellybutton-bearing dress that didn’t leave much to the imagination. Even more talked about was her colorful hair. “This was a point in my life when I wanted to have braids, when I wanted to be able to be unafraid to experiment,” she said.

10 of 50

ELECTRIC YOUTH

ELECTRIC YOUTH
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From the ponytail on top of her head to the hot-pink bubble skirt, Debbie Gibson looked like a picture-perfect bubblegum pop star in 1988.

11 of 50

RED DRAGON

RED DRAGON
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Although Sisqé – famous for the “Thong Song” – didn’t show up in underwear, he did grab attention for this studded fire-engine red ensemble in 2000.

12 of 50

RAP BATTLE

RAP BATTLE
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Elton John and Eminem came together in 2001 – in a polka-dot suit and baggy sweatpants – to perform Eminem’s hit “Stan,” despite protests by gay activists who called the rapper homophobic. Nevertheless, Eminem picked up two awards that night, while Elton received one.

13 of 50

PRIVATE DANCING QUEEN

PRIVATE DANCING QUEEN
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Triple winner Tina Turner – whose trophies included record of the year for “What’s Love Got to Do with It” – brought down the house in 1985. “I’ve lived it,” Turner told Ebony of her famous comeback. “My wildest dream, after I got my divorce, was for all of this to happen … to walk out onstage to that many people who came to see me, to know what that feels like. Now, that’s a dream!”

14 of 50

ASIAN FUSION

ASIAN FUSION
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In her Geisha girl phase in 1999, Madonna opened the show in this flame red kimono. That rendition of “Ray of Light” kicked off a big night for the singer, who won her first Grammy and eventually took home three awards. “I’ve been in the music business 16 years,” she said in her acceptance speech. “This is my first Grammy … but it was worth the wait and all that.”

15 of 50

WINNING SUIT

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Today, he’s rarely seen without his signature shades and black ensemble, but back in 1988, a mulletted Bono was a funky mix in a colorful tie and top hat. At the show, U2 received their first-ever Grammys (for The Joshua Tree) and have since won a total of 22.

16 of 50

THE BRAIDY BUNCH

THE BRAIDY BUNCH
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Before they were stripped of their 1990 best new artist award and dropped from their label, the multiplatinum lip-synching duo Milli Vanilli – Rob Pilatus and Fabrice Morvan – made Grammy night a colorful one. Eight years later, Pilatus died of a suspected drug and alcohol overdose. As for Morvan, he is attempting a solo career, marketed through his MySpace page.

17 of 50

TUTU MUCH

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Looking like Peaches ‘n Cream Barbie, Britney Spears attended her first Grammy Awards in 2000 in a sea of sherbet-colored tulle. She didn’t go home a winner that year, losing best new artist to fellow Mickey Mouse Club alum Christina Aguilera, sparking more rumors of a rivalry.

18 of 50

SPARKLE IN HER EYES

SPARKLE IN HER EYES
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It was eyes wide shut for Alicia Keys in 2002, a winner of five awards that night. The singer’s lids were so overloaded with eyeliner, false lashes and rhinestones, she could barely keep her eyes open.

19 of 50

BALLAD OF JOHN AND YOKO

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AP

In the early stages of pregnancy with son Sean, Yoko Ono covered up in a boa when she accompanied John Lennon to the 1975 Grammy Awards. As for the ever-quirky Lennon, he dressed head-to-toe in a velvet suit, accessorized with an Elvis pin and a button with one of his pseudonyms, Dr. Winston O. Boogie.

20 of 50

FLOWER POWER

FLOWER POWER
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In 2005, nominee Joss Stone planted herself on the red carpet in this busy Petro Zillia gown.

21 of 50

SINGING THE BLUES

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Celebrity Photo

Fresh-faced newcomer Whitney Houston looked cool and crisp in a simple blue gown when she picked up her first Grammy in 1986 (for her hit “Saving All My Love for You”).

22 of 50

FIT TO BE TIED

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Ron Galella/WireImage

Not only was Rick Springfield practicing medicine on the soap opera General Hospital in 1982, but he was also burning up the charts with his No. 1 hit “Jessie’s Girl.” At the Grammys that year, the heartthrob was tickled pink – accepting his first and only award in a pink plaid blazer and matching tie. Swoon!

23 of 50

GO-TO GUYS

GO-TO GUYS
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Known for their offbeat performances (singing on treadmills!), Grammy winners OK Go went incognito in 2007, in patterned suits and gloves with purple masks. “We’re dressed in the future – the future dressed us,” one obfuscated band member told PEOPLE, adding, “This is actually us in an hour.”

24 of 50

THE 411

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In 1996, Mary J. Blige picked up her first Grammy in a hooded leopard-print getup – complete with shades. “I think she’s changed fashion,” her stylist Misa Hylton-Brim later said. “Her realness makes her.”

25 of 50

BLOCK PARTY

BLOCK PARTY
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Although they weren’t nominated for any awards, the original boy band – New Kids on the Block – were hangin’ tough as presenters in 1990. This year, Jonathan and Jordan Knight, Donnie Wahlberg, Joey McIntyre and Danny Wood have since decided to reunite for a comeback.

26 of 50

MILLENIUM MEN

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Taking a page from the New Kids, the Backstreet Boys – Howie Dorough, Nick Carter, A. J. McLean, Kevin Richardson and Brian Littrell – suited up in coordinated outfits in 1999, when they were nominated for five Grammys, including album of the year.

27 of 50

LABEL CONSCIOUS

LABEL CONSCIOUS
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Resembling a few of Jessica Simpson’s handbags stitched together, rapper Nelly hit the 2001 Grammy Awards in a Louis Vuitton suit, baseball cap and sneakers.

28 of 50

CUTTING EDGE

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TRAPPER FRANK/CORBIS

At the 2000 ceremony, Missy Elliott cut a sharp figure on the red carpet, in a purple pantsuit trimmed with razor blades.

29 of 50

BLONDE AMBITION

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In braids and a Bindi, Gwen Stefani (then still the frontwoman for No Doubt) reaches out to Courtney Love – in a sheer gown! – at the 1998 awards.

30 of 50

MATCHY, MATCHY

MATCHY, MATCHY
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At the 1977 Grammys, Barbra Streisand was a true golden girl in a coordinated gold gown, wrap and choker. The music and screen legend picked up two awards, including best song for “Love Theme from A Star Is Born”.

31 of 50

HIP CHECK

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In 2001, best R&B vocal performance winner Toni Braxton decided to show a little leg – and then some! – in this skimpy Richard Tyler number. “I chose the dress because I just got married two months ago, and I wanted to wear something very sexy,” she said at the time. Mission accomplished.

32 of 50

THE INGENUE

THE INGENUE
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In 2007, Scarlett Johansson – who appeared in nominee Justin Timberlake’s video for “What Goes Around Comes Around” – got photographers snapping when she arrived in this Monique Lhuillier little black dress.

33 of 50

VIVA RICKY!

VIVA RICKY!
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Bon Bon shaker Ricky Martin was the It boy in 1999, thanks to a bombastic rendition of his song “La Copa de la Vida” – and those leather pants. Even Madonna was intrigued by the best Latin pop performance winner, sneaking up behind him in the press room and covering his eyes as he talked to reporters.

34 of 50

NOTHING COMPARES

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Although she didn’t rip up any photos of religious icons – she saved that for Saturday Night Live – performer Sinéad O’Connor still commanded attention with her sports bra, ripped jeans and painted, shaved head in 1989.

35 of 50

SIMPLY THE CHEST

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Nothing like a little chest hair to get the evening going. Best rap album winner Kanye West had disco fever in his unbuttoned shirt, gold medallions and white jacket at the 2006 show. It was one of seven outfits suggested to the rapper by Yves Saint Laurent designer Stefano Pilati.

36 of 50

KISS AND MAKEUP

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It was a pasty-faced KISS reunion when all four original members of the band – Gene Simmons, Peter Criss, Paul Stanley and Ace Frehley – got together for the 1996 awards. It was the first time the four appeared together in full regalia since Criss quit the group in 1980.

37 of 50

BOTTOM LINE

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Leaving her skirt at home, hip-hop diva Lil’ Kim left little to the imagination in 1998 when she arrived in black beaded panties, sparkling tights and a sheer, floor-length shawl.

38 of 50

DESIGNING MEN

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Corbis

Only at the Grammys can cutoffs and a vibrant green suit – on 1999 rap nominees Andre 3000 and Big Boi of OutKast – be paired together on a red carpet.

39 of 50

LET IT GROW

LET IT GROW
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In 2006, nominee Imogen Heap sprung up in this unique ensemble designed by a fan who contacted her on MySpace. Her nature-themed getup included a lily-pad covered dress, a potted plant in her hair, parasol and – to bring it all together – a frog in hand. “It took me 40 minutes [to get ready],” she told a reporter. “[The plant has] been in my hair all day … and still growing.”

40 of 50

COLORS OF LIFE

COLORS OF LIFE
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Wearing an earth-toned gown of her own design – and carrying a large satchel in lieu of an evening bag – nominee Erykah Badu was statuesque (and practical) in 1999. “I believe each woman should have her own personal wrap, her own personal style,” the singer has said.

41 of 50

BELLY ACHE

BELLY ACHE
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In 2005, nominee Sheryl Crow called attention to her toned abs in a yellow halter dress with a peekaboo cutout. As for accessories, she had a LiveStrong bracelet – the $1 rubber band that raises money for cancer research through the Lance Armstrong Foundation – on one arm, and then-beau Armstrong on the other.

42 of 50

THAT'S A WRAP

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Long before Jada Pinkett Smith fronted the metal band Wicked Wisdom, she wrapped up in a lighter look in 1999, with a head wrap, tummy-exposing dress and ballerina-style heels.

43 of 50

SILVER LINING

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Celebrity Photo

Try as they might, nobody could touch MC Hammer in 1991. For music’s biggest night, the rapper ditched his trademark “Hammer pants” for a silver jacket and boots and picked up three awards for his album U Can’t Touch This.

44 of 50

MAN IN THE MIRROR

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While accepting the Living Legend Award in 1993, Michael Jackson delivered a sad speech about growing up a star, saying, “My childhood was completely taken away from me. There was no Christmas. There were no birthdays.”

45 of 50

SCHOOL DAZE

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Garbage singer Shirley Manson hit the books in 2000, dressing as a schoolgirl in a plaid skirt, patent leather shoes, button-down and tie.

46 of 50

PURPLE REIGNED

PURPLE REIGNED

Buttoned into tight-fitting lace pants and a matching off-the-shoulder shirt, Prince went crazy at the 1985 Grammys – the year Purple Reign won.

47 of 50

SKIRTING THE ISSUE

SKIRTING THE ISSUE
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Veteran musician Sting tried out a kilt instead of, say, trousers in 2004, the year he picked up an award for best pop collaboration with vocals for his duet with Mary J. Blige on “Whenever I Say Your Name.”

48 of 50

HALF AND HALF

HALF AND HALF
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Pink got a leg up on the competition in 2002, winning the Grammy for best female pop vocal performance in a garter, bowtie and one pant leg.

49 of 50

PRINCE CHARMING

PRINCE CHARMING
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By 1992, “Fresh Prince” Will Smith was already a trailblazer: He won the first-ever Grammy in the rap category in 1988, and was starring on a hit sitcom, The Fresh Prince of Bel-Air.

50 of 50

ROCK THE BOAT

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Best new artist nominee Avril Lavigne (in Converse sneakers and a skull belt buckle) played designer in 2003, taping the words “Rock On” into her suit jacket.

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