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The Wildest Looks From the Grammys Red Carpet

From Lady Gaga to Lil’ Kim, outlandish style from Music’s Biggest Night

Grammy Fashion


This Monday, an elite selection of musicians will descend upon Los Angeles for the 58th Annual Grammy Awards. And because the music world is such a wacky place, those musicians are also style icons. To psych ourselves up for the triumphs and disasters that will surely endure, we took a look back at some of the wildest, weirdest, and most sartorially reprehensible moments from past Grammys. Come, let's stroll down this unwieldy red carpet. By Julianne Escobedo Shepherd

See all of Rolling Stone's Grammy coverage here!

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When you're standing next to Courtney Love in fluffy boudoir shoes and you're the hot mess, you know you're in trouble. This was the era we like to forget in the legacy of fashion icon Gwen Stefani: the bindi-and-rows era, OG cultural appropriation. The ombre/tie-dye maxi-skirt isn't helping her cause.

Grammy Fashion: 2000: Jennifer Lopez

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This is the dress that changed it all for Jennifer Lopez — the low-cut widely credited for bumping her career to megastardom. And it's probably good that the cut's so low, because it's distracting us from the fact that the pattern and material of the garment are those of a poolside chemise for a Miami retiree. 

Grammy Fashion: 2001: Christina Aguilera



This look was during Christina Aguilera's peak pirate phase — you know, when she was dressing like sexy Captain Jack Sparrow — so frankly, it could have been worse. It's not that the cut doesn't look phenomenal on her, but the front-tie, front-slit, strappy sandals, mauve, and rows is the definition of "doing too much."

Grammy Fashion: 2001: Justin Timberlake and Joey Fatone

Photo: Micelotta/Getty


You know, you have to give Justin Timberlake credit: even in hideous green velvet and a tie that looks borrowed from J. Edgar Hoover, he really knows how to choose a suit that fits him. Fatone matched his tie to his collar to his highlights, so that's something, too. Let us never revisit this era.

Grammy Fashion: 2001: Toni Braxton



You can't blame Toni Braxton for flaunting it: she is a Sculpted. Goddess. Plus, she presaged this year's butt-baring trend by over a decade. Your move, Gwyneth

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Lil' Kim don't stress em! That pose she's making with her hand is one, as in Formula One. Quite unsure about the choice of the baby blue driving glove when the ensemble is fire-engine red, but she did an impeccable job of color-coordinating to the carpet and the Grammys backdrop. That's how you do a step and repeat.



How do you know your groupmate is about to disband and go solo? She stops matching her ensembles to yours. Beyoncé's purple hues against the black Kelly and Michelle are wearing says, "I am the Diana Ross."

missy elliot

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Missy Elliot's Under Construction vibe was full-force throwbacky, and in this fresh Adidas ensemble with matching angora Kangol, you could have caught her at a park jam circa 1984. Wish her date had been Cam'ron

Grammy Fashion: 2007: Ok Go

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. . .And yet, does Yeezus know that OK Go did the mask thing six years before he did? Granted, they're certainly not Margiela, but still. Sidebar: this is so, so creepy. 

Grammy Fashion: 2007:Imogen Heap



Imogen Heap is the type of artist who can do a true Helena Bonham-Carter in Sweeney Todd and look both intentional and stunning. This look is not for everyone, and we could do without the daisy appliqués, but she pulled it off. The grass is in her hair, and maybe in her system. 

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M.I.A. flaunting her extreme pregnancy in a sheer Henry Holland dress remains one of the greatest Grammy moments ever, especially because she performed in it alongside a slew of rap royals wearing formal suits, while those of us watching at home were terrified her water would break during the performance. This is so bossy. 

Grammy Fashion: 2009:M.I.A.



. . .and she even had a costume change! This blue Manish Arora dress both hid and emphasized her giant baby bump, and let us know, as ever, that M.I.A. did not give a hoo what we thought of her. 

Kevin Mazur/WireImage


E Pluribus Unum: Lady Gaga did the damn thing and will do it again. Here she's dressed as the ice goddess that Major Tom met when he stepped into the light. 

nicki minaj

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"Monster"-era Nicki Minaj hearkens back to Mary J. Blige's cheetah gown with a Bride of Frankenstein twist. She's going for more demure looks now, and frankly we miss the days of Minaj fashion risks. No one does it quite like her.


Jeff Vespa/WireImage


A rare moment of Rihanna not looking flawless — something about the neckline is bulky and she looks overwhelmed. Nonetheless, stripes in feathers-and-sheer give her the gait of a beautiful swan. Go forth, Rihswanna!

Kelly Rowland

Steve Granitz/WireImage


Kelly Rowland's knockout sheer paneling was brave — you could imagine one wrong move and the whole of it would spill out — but it underscored that K-Row doesn't get enough credit for her style. Very chic.

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