When it comes to red carpet faux paus, most minds turn to Icelandic singer Bjork’s swan dress (and matching egg purse!) from the 2001 Oscars, which she attended as a best original song nominee for her contribution to the dramatic musical “Dancer in the Dark.” But Bjork’s gown, which came from the mind of Macedonian designer Marjan Pejoski, isn’t the only red carpet misstep. Whether their outfits are art pieces gone awry, cries for attention or just ill-fitting, several celebrities have worn iconic fashion disasters at award shows.
Cher, 1986 Oscars
Cher has never been one to play it safe, and this sparkly, spiky, stomach-baring design from long-time collaborator Bob Mackie was no exception. Cher was attending the 1986 Oscars as a presenter for best supporting actor, but it would have been more fitting for her to present best costume design.
Gwyneth Paltrow, 2002 Oscars
A few years after making waves by accepting her 1999 Oscar in a girlie, pink Ralph Lauren gown, Gwyneth Paltrow went goth in a dark, sheer Alexander McQueen gown at the 2002 Oscar red carpet. The pastel Lauren gown still gets mixed reviews, but everyone agrees that even the small-busted Paltrow could have benefited from a bra with the McQ.
Lil Kim, 1999 MTV Video Music Awards
Sticky or just plain tacky? Rapper Lil’ Kim wore her purple pasty (sometimes referred to as her sticky) to the 1999 VMAs, where she was famously groped on stage by singing diva Diana Ross. More than a decade later, her attire was still shock-worthy enough to win MTV’s Wildest VMA Outfit audience poll.
Angelina Jolie, 2012 Oscars
Angelina Jolie’s sexy Atelier Versace outfit meant well, but it’s the way the actress-director wore the dress at the 2012 Oscars that makes it memorable. Her constant need to show off her toned right leg made her a joke at the awards show when “The Descendants” screenwriters mocked her pose after she announced them as the adapted screenplay award winners. At home, parody Twitter handles and Internet memes were born.
Lara Flynn Boyle, 2003 Golden Globes
“The Practice” actress Lara Flynn Boyle didn’t leave much to the imagination when she donned a David Cardona tutu for the 2003 Golden Globes. The ill-fitting ensemble (how often is a leotard too baggy?) also didn’t help the Hollywood gossip surrounding her rapid weight loss and her recent breakup from Jack Nicholson.
Whoopi Goldberg, 1993 Oscars
Sometimes it’s hard to choose between pants or a dress. For the 1993 Oscars, comedian Whoopi Goldberg wore both. The skirt of her vibrant purple gown could be pulled back to reveal a skin-tight aqua pants suit. Still, points should be awarded for finding one pair of shoes to match both looks.
Britney Spears and Justin Timberlake, 2001 American Music Awards
Whether it was done for irony, as a nod to their Southern roots or just as a way to get through yet another award show, then-couple Britney Spears and Justin Timberlake wore matching denim ensembles to the 2001 American Music Awards. Timberlake, at least, has grown out of the shock-and-awe phase of his sartorial career. He co-founded the William Rast clothing line and is routinely on menswear critics’ best-dressed lists.
Lady Gaga, 2010 MTV Video Music Awards
Lady Gaga has said that her Franc Fernandez-designed meat dress for the 2010 VMAs was meant to be a statement on the nature of celebrity (not, mind you, one about vegetarianism). That’s fine, but it’s not very original -- the “Los Angeles Times” points out that artist Jana Sterbak made a similar statement with “50 pounds of raw flank steak, stitched together into a slowly rotting garment and displayed” in 1991.
Demi Moore, 1989 Oscars
Demi Moore was at the height of her fame when she walked the red carpet at the 1989 Oscars. So it’s shocking that someone so powerful didn’t want a designer label to dress her on the big night. This is a shame because anyone -- even then-husband Bruce Willis -- would have probably come up with something better than a bustier and bike shorts with a gold-and-red-patterned train.
Geena Davis, 1992 Oscars
We can’t be too hard on costume designers Ruth Meyers and Bill Hargate, who created the frilly white gown supporting actress nominee Geena Davis wore to the 1992 Oscars. After all, model-actress Stephanie Seymour wore a similar look a few months later in the video for Guns N’ Roses’ power ballad “November Rain.” Perhaps the look was just en vogue?
Whitney Friedlander is an online and print journalist whose work has appeared in "Los Angeles Times," "LA Weekly," and "Los Angeles" magazine. She writes about fashion, home & garden, lifestyle, celebrities and more. She received her bachelor's in journalism from University of Missouri in 2002.