The Most Outrageous Grammy Looks Of All Time

Pop culture’s rebuttle to the unanimous complaint uttered by critics after every award show “no risk takers!” is, without a doubt, the Grammy Awards. In all of their flashy, fleshy splendor, the Grammys promise to deliver a parade of international stars in controversial outfits, allowing us a peek into their wildest sartorial fantasies. (Or at least those of their stylists).

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    And the winners of our favorite all-time, jaw-dropping, gasp-inducing, outfits are as follows:

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    PHOTO: Frank Micelotta/ImageDirect

    Destiny's Child 2001:

    As with most of Destiny’s Child’s outfits, we can thank Tina Knowles for these spangly get-ups. We particularly appreciate that they are coordinated, but not identical: it really keeps the eye moving. They switched to equally stunning bright green, sequined camo looks to accept the five awards they took home that evening.

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    PHOTO: Scott Gries/ImageDirect

    J. Lo 2000:

    Who can forget the epic $15,000 Versace stunner worn by J. Lo when she accompanied P Diddy to the 42nd Grammy Awards? The vivid tropical green fabric and exaggerated plunging neckline have made it one of the most memorable dresses in red carpet history. So much so that Trey Parker of South Park wore an imitation of the dress to the 72nd Academy Awards.

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    PHOTO: Dan MacMedan/WireImage

    Lady Gaga 2010:

    Before the meat dress and arriving in an egg, Gaga wore this intergalactic ensemble by Armani Prive. Credit here is due primarily for her ability to maintain balance—note the platform, heel-less, sock boots and the dress that appears to be in orbit—but secondly for not spearing any fans, photographers or attendees with whatever she is holding in her hand. Although she did perform “Poker Face” alongside Elton John that evening…

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    PHOTO: Jeff Kravitz/FilmMagic, Inc

    Kanye West 2006:

    Before taking the stage to perform “Gold Digger” (for which he won Best Rap Solo Performance) alongside Jamie Foxx and a marching band, West walked the carpet in this Scarface ensemble, complete with chest hair and gold pendant. A full eight years later, West has 21 Grammys under his belt and is currently nominated for Best Rap Song for “New Slaves”, and Best Rap Album for Yeezus.

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    PHOTO: Kevin Mazur/WireImage

    Britney Spears 2002:

    The simple red gown showed off her enviable figure, but it’s Britney Jean’s fountain of curls that deserve accolades. We’re not sure how her neck fared the next day, but we applaud her for deviating from the flat-ironed hair of that era.

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    PHOTO: Dan MacMedan/WireImage

    Coldplay 2009:

    The 2009 Grammy Awards were pretty memorable for Coldplay frontman Chris Martin. His band scooped up the coveted Song of the Year, Best Pop Vocal Performance By A Duo Or Group, and Best Rock Album awards, wowed the audience with their performance of “Viva La Vida”, and he even performed a duet of “Lost” with Jay Z. Characteristic of his British manners, he also apologized to Sir Paul McCartney for these Sgt Pepper-inspired outfits.

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    PHOTO: SGranitz/WireImage

    Toni Braxton 2001:

    After J. Lo came the deluge. The following year, Toni Braxton slipped on this white, Richard Tyler number to collect her Best Female R&B Vocal Performance award. Braxton told People magazine: “I’ve always gone a little risque with all my other awards [show outfits], I decided that before I got married and had babies, I'd wear this” which is coincidentally the only way to look at this without getting an eyeful.

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    PHOTO: Getty Images

    Cindi Lauper 1984:

    If this outfit doesn’t sum up the ‘80s, we’re not sure what does. While Michael Jackson was collecting Album Of The Year for Thriller, Lauper was hamming it up with Rodney Dangerfield, sporting Ziggy Stardust cheekbones, gold lipstick, and a tropical lame outfit best described as Miss Cleo goes to Vegas. She took home Best New Artist the following year.

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    PHOTO: L. Cohen/WireImage

    Ok Go 2007:

    The year that they won the Best Short Form Music Video for the dizzying treadmill stylings of “Here It Goes Again,” Ok Go appeared on the carpet in matching outfits that should probably have been left at home (specifically over the windows). Extra points for the printed accessories and for having the modesty to remain faceless.

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    PHOTO: Jeff Kravitz/FilmMagic

    Cee Lo Green 2011:

    This plumage is actually the physical incarnation of the uplifting song “Forget You” that he performed with an impressively stage savvy Gwyneth Paltrow. While Paltrow lithely balanced atop the grand piano for her Grammy performance debut, Cee Lo shimmied with an army of muppets. In a simple black jumpsuit, Paltrow still stole the show. 

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    PHOTO: Gregg DeGuire/FilmMagic

    Rihanna 2011:

    Rihanna donned a fluffy Jean Paul Gaultier confection for the 2011 awards. While the strategically placed stripes work when she is standing up, we can’t help but wonder how effective they were when she was walking, climbing stairs or just sitting down.

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    PHOTO: BEImages/Dan Steinberg

    R. Kelly 2004:

    Sadly Kelly did not take home either of the awards he was nominated for in 2004, but it was the year that he released Unfinished Business with Jay Z and continued to enjoy the success of his 2003 album Chocolate Factory, so it wasn’t all tears. This particular get-up seems to foreshadow the skulking and being trapped in the closet that would mark his career in the coming years.

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    PHOTO: REX USA/Picture Perfect

    Nicki Minaj 2012:

    With a Papal-esque figure as her date, Minaj selected a Versace cape, gloves, and blonde wig for both her red carpet and performance ensemble. It made a little more sense once she took to the stage amongst dancers dressed as monks and choir boys, but then it devolved into an exorcism of her alter ego, Roman, and we were left as bemused as ever.

EXPLORE: Celebrity Style, Beyonce, Destiny's Child, J. Lo, Lady Gaga, Kanye West, Britney Spears, Coldplay, Cindi Lauper, OK Go, Cee Lo Green, Rihanna, R. Kelly, Nicki Minaj
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