Worst Oscar Dresses Of All Time

In making her grand entrance at the 1989 red carpet, Demi Moore broke the cardinal rule of red-carpet fashion: leave the bike shorts at home. The "Ghost" actress continued her plummet into fashion notoriety by finishing off her ensemble with an ill-fitting leotard and a bustier-skirt combination that bore a striking resemblance to couch upholstery. While it remains uncertain whether Demi got lost on her way to the gym, ballet class, or a bizarrely floral-themed party, the outfit was wildly inappropriate for Hollywood’s biggest night – or any night, for that matter.
From its very asymmetrical neckline to the tacky gold print that runs down the dress’ one jacket sleeve, Kim Basinger’s dress at the 1990 Oscars made her look more like a drunk Disney princess than a well-respected actress. To make matters worse, she then added a long white glove so tight that it prompted viewers to wonder how she broke her arm. Unfortunately, Kim designed the overly shiny, cheap-looking satin confection herself and then chose to mix it with a stringy blonde hairstyle and overly red lipstick. Missing the mark on all counts, Kim appears to have gotten lost in the slums on her way to the ball.
The fact that Whoopi Goldberg chose to don a fluorescent purple and green suit-dress to the 1993 Oscars should speak for itself. Whether the comedienne was trying to stir up a laugh or attempting to serve as Kim Basinger’s equally intoxicated fairy godmother, there is no excuse for her highly misguided ensemble.
Although Cher was apparently known as the Lady GaGa of her generation for her tendency to wear outrageous outfits, her Bob Mackie-designed spiky bra, skirt, and headdress would have been extremely inappropriate for the MTV Video Music Awards, let alone the 1986 Academy Awards. Judging by the bar-like netting on her choker, bracelets, and necklace-like upholstery, Cher knew this ensemble, which she finishes off with a Professor Snape cloak, would get her arrested by the fashion police. Yet, the fact that she could fit about fifteen Academy Awards in that monstrous headdress serves as a testament to the utter ridiculousness of this bewildering outfit.
Try as they might, however, no actress has yet managed to steal the bad-fashion crown from Bjork. The Marjan Pejowski swan dress that she donned for the 2001 red carpet has become more famous – or infamous – than the performer herself. The reason why Bjork decided to drape a swan, beak and all, around her neck and wear it to America’s most prestigious awards ceremony remains a mystery. One thing is certain, however: one glance at the animalistic ensemble invoked pity within viewers feeling bad for the humiliated swan.
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Comments
You said that Bjork's reason for wearing the swan dress "remains a mystery" but that is false. She actually had a well lasting obsession with swans and had a heavy association to them with romance. Her album cover for Vespertine was based on that whole white winter, lovey-dovey (or swan in this case) vibe. She's actually wearing the swan dress on the album cover too! Oh, and you forgot to mention the egg purse. You know, that purse she brought with her to lay on the red carpet out from under her dress. It was rather charming. It can be fun to dump on her for fashion, but it really doesn't boil down to fashion at all. When people put this dress and Bjork under a microscope of fashion, she's being taken completely out of context. She's not oblivious to fashion at all either, she just REALLY doesn't give a damn. She sold the dress for charity, by the way.
Alot of these dresses are actually very fashion forward. I'm kind of disappointed that someone just fell back onto other people's opinions of what style should be according to the trends...under the guise of fasion "journalism." I don't know whether to point the finger at the writer who adopted everyone else's demeaning responses to the outfits, or the unimaginative editor who assigned. Both of you missed the mark of what fashion writing is all about.
*fashion. My apologies for the misspell.