The Wildest Looks From the Grammys Red Carpet - Rolling Stone
Home Music Music Lists

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!

Grammy Fashion: 1975:Bette Midler and Stevie Wonder



Bette Midler and Stevie Wonder made the best dates for their equal Grammy-ensemble chutzpah: Stevie redefines the "denim tuxedo" by actually wearing a denim tuxedo, while Bette's function 45-as-hat and sparkly applique screams "2 AM at Studio 54"— which is no doubt where they're going after this. 

Grammy Fashion: 1983: Grace Jones

Photo: Walter/WireImage


Grace Jones needs no addendum to her badassery, but here's one that underscores it: She can enter a Pier 1 Imports and find an accessory, no problem. That head-basket: a new definition of "weave." 

Grammy Fashion: 1984: Brooke Shields, Michael Jackson, and Emmanuel Lewis



Brooke Shields, Michael Jackson and Emmanuel Lewis. This is here to remind you that Michael was never a sartorial slouch: a sequined military sash requires matching effing socks, y'all. 

Grammy Fashion: 1984: Cyndi Lauper



This is, of course, a color story: parrot green, misty purple, pineapple yellow. Somewhere deep down, we like to think Cyndi Lauper's Grammy sass influenced Prada's legendary Spring 2011 collection, bananas and all

Grammy Fashion: 1985: Naomi Judd and Wynonna Judd

Photo: Galella/WireImage


Calling it now: Dressing like your mom is gonna be hot for 2014. Naomi and Wynonna Judd's matchy-matchy slash gowns in contrasting hues express that it's an unequivocal family affair. 

Jim Smeal/WireImage


Smack in the middle of the grunge era, Arik Marshall, Chad Smith and Flea of the Red Hot Chili Peppers wore sophisticated black, bucking the no-shower trends of their northwesterly counterparts, while Anthony Kiedis wore some kind of gilded hakama and accessorized his nether regions with his Grammy. Sometimes a little can be so much.

Grammy Fashion: 1995: Annie Lennox



She was 41 when she attended the Grammys dressed as Minnie Mouse, and she can do anything she damn well wants because she's Annie Lennox. Go ham, Annie. Do you.

Grammy Fashion: 1996:Mary J. Blige



The original cheetah girl, Mary J. Blige, doing gloves and indoor sunnies because she just won a Grammy for My Life and also invented the hip-hop R&B collabo. Too bad Method Man wasn't there in a man version of this super sophisticated look.

Richard Corkery/NY Daily News Archive via Getty Images


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

Photo: Vespa/WireImage


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

Frederick M. Brown/Getty Images


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

Evan Agostini/Getty Images


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

Dan MacMedan/WireImage


. . .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. 

Steve Granitz/WireImage


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

Jeff Vespa/WireImage


"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.

In This Article: Lady Gaga

Arrow Created with Sketch. Calendar Created with Sketch. Path Created with Sketch. Shape Created with Sketch. Plus Created with Sketch. minus Created with Sketch.