Oscars Fashion Disasters

Over a generation, citizens of popular culture have watched as a fundamental source of pleasure has vanished from view: the red-carpet fashion “disaster.” (I use the scare quotes because disaster is the accepted shorthand but the wrong word—the accurate term would be something like “Red-Carpet Fashion Deviations from an Established but Somewhat Arbitrary Norm.”) Especially at the annual Academy Awards ceremony, the stakes have become so high for actresses and their reps that emergency-management teams of stylists, groomers and go-to designers have all but foreclosed the possibility of true catastrophe.

This is unfortunate. A functioning Oscar-fashion ecosystem should not consist solely of elegant swans—it also needs an occasional Swan Dress. (For real, does anyone remember anything about the 2001 Oscar ceremony other than Björk’s Swan Dress?) But the highly polished awards season thus far holds out little promise that a challenger to the Can-Can Mullet (Geena Davis, 1992) or the Plus-Size Backward Pantsuit (Céline Dion, 2000) will emerge during the awards on Sunday, Feb. 24.

So this list is a look back at a mostly extinct phenomenon, and like any endeavor tinged with grief, it is highly subjective and slightly irrational. It begins near the turn of the 1990s, a fertile era for Oscar fashion disasters but one not too far removed from the homogenizing advent of the professional stylist. It values a sense of humor, and privileges the explosively weird over the merely unfortunate. (Or the literal-minded: Faith Hill’s Rainbow Sherbet gown of 2002 was on the list until I remembered it was the same year she sang “Over the Rainbow.”) It does not include Cher, because Cher is a concept with its own norms from which Cher-qua-Cher cannot deviate. Most importantly, for me at least, is that most of these ensembles are fascinating not for what they are but for what they represent: the vertiginous threshold space between idea and result, between what you see in the mirror at home and the mirror the world then holds up to you.

Demi Moore - 1989

It has been said that stars no longer style themselves because of what happened when Moore tried it. Yet just the following year, Kim Basinger also showed up to the Oscars in a self-designed ensemble: white satin ball gown and matching asymmetric jacket with gold trim, topped with chlorine-permed hair, evoking Madison from Splash as the Bride of Sgt. Pepper. Basinger’s design was basically coherent; Moore’s had no such problem. The bustier, the domed skirt, the Holbein-ish embroidery, the lace-trimmed exercise shorts—it’s like someone locked her in the Tower of London for months with nothing but a stationary bike and a mood board for company, and the mood board became self-aware. Something like this outfit will not happen again anywhere near the Oscar ceremony, and Moore’s then-husband Bruce Willis seemed to sense the gravity of the occasion; his signature Stoic Grimace™ found an ideal context here.

Mia Maestro - 1999
Nominated for Elizabeth, Cate Blanchett arrived to the 1999 ceremony in an instant-classic violet gown embroidered with flowers and, perched on her back, a gorgeous hummingbird. Supposedly, the same man who made that immortal dress, John Galliano of Dior, was also responsible for Maestro’s look that year. Her ensemble does capture the everything-but-the-kitchen-sink millennial Galliano aesthetic much more than Blanchett’s, but I remain unconvinced that this dress wasn’t the product of a proto–Project Runway craft-store challenge. Or hey, remember in Pretty in Pink, when Harry Dean Stanton gives Molly Ringwald two ugly dresses and she has to make one pretty dress out of them? I think maybe it was that kind of situation, except in this case Maestro had a roll of wallpaper, a bunch of faux fruit from Linens ’n Things and a scarf I bought in Oaxaca, and she still hit the red carpet looking as confident as if she were wearing the other Galliano dress.
Angelina Jolie - 1999
The consensus was that Jolie came dressed as Morticia Addams, but Morticia Addams showed more cleavage and didn’t canoodle with her brother. I think Jolie came as a brilliant personification of the climactic scene in Girl, Interrupted (for which she won her Oscar that night) in which Winona Ryder tells her that she is dead inside. Dress by Gucci, hair extensions by Elvira, general affect by Monica Bellucci in Bram Stoker’s Dracula.

Bjork - 2001


Yoko Ono once asked, “Do you ever hate a cloud?” Hating this dress is like hating a cloud. Natalie Portman should have worn a maternity version of it when she won for Black Swan, and dedicated her award to Björk. This dress is why I watch the Oscars.

Uma Thurman - 2004
Thurman rarely places a foot wrong on the red carpet, and glided ahead of the curve when she draped herself in diaphanous lilac Prada in 1995. Yet in 2004, year of Kill Bill, the actress perpetrated what may be the last-ever bona fide Oscar fashion disaster—but she staged it willingly, much as Michael Bay stages a disaster movie. “We’ve gotten so savvy with stylists that’s a kind of warfare of defensive dressing out there,” explained Thurman, who plucked her Swiss Miss–in-a-nightgown look straight off Christian Lacroix’s runway. “Everyone looked the same. Everyone had it down to such a perfect T…You get bored. That’s when you have to say, ‘I will be worst-dressed.’” It’s been nine years, and nobody’s said it since.

Celine Dion and Gwyneth Paltrow at the source.

So, in your opinion, which are worst/best Oscar dresses of all time?