FLASHBACK: The 9 most memorable Oscar dresses

Back to story February 19, 2015

While the outfit she wore to the Academy Awards two years later would be immortalized in wax, Cher turned heads at the 1986 Oscars in a black sequined, showgirl-worthy number by Bob Mackie with a rooster-feather headpiece that added two feet to her already statuesque frame. With its caged neckline, bared midriff and slouchy evening jacket, we could almost see Rihanna rocking this look today (Met Ball 2014, perhaps?).

One fashion term you don’t hear often when talking about the Academy Awards is “bicycle shorts,” but Demi Moore – on the arm of then-husband Bruce Willis – broke all the rules in 1989. The 'Ghost' actress took a chance on an unknown designer: herself! The result? A gold lamé bustier peeked out from beneath a black embroidered corset with long sleeves, giving way to a matching lamé-lined train and lace-edged bicycle shorts.

Whoopi Goldberg was ahead of her time in 1993, calling to mind the skin tone of yet-to-be-created animated icon Shrek, and we think the Oscar winner could give lessons in turning heads. Plus, the Sister Act star was nothing if not coordinated: from her purple-and-lime coatdress to her embroidered purple-and-lime jumpsuit right down to her – you guessed it! – purple-and-lime pumps. Care for a closer look? The vibrant ensemble is on loan to Planet Hollywood in New York.

At the 1996 Oscars, Sharon Stone took “effortlessly chic” to a whole new level! As speculation raged over who would dress the Casino nominee, Sharon grabbed a grey Gap turtleneck from her closet and paired it with a Valentino skirt and Armani coat. Talk about a high-low mix! We wonder whether Sharon’s high street sensibility inspired Helen Hunt’s H&M gown choice at the 2013 Academy Awards.

Canadian chanteuse Celine Dion made fashion history in 1999 by flipping the switch on suiting, giving the red carpet some serious back action in a white tuxedo with a backwards jacket. The crowning touch on her John Galliano for Dior look was a white chapeau shaped with a sharply curved, asymmetrical brim. Fashion panels the world over have debated this look since it first graced the carpet, but we applaud Celine’s willingness to take a risk!

Even if you’re not a fashion person, you’ll remember that time that Bjork put a bird on it. In fact, the “Swan Dress of Bjork” has its own Wikipedia page. The year was 2001, and the avant-garde Icelandic singer graced the red carpet hot on the heels of an Oscar nomination in 2000. The unusual dress, designed by Marjan Pejoski, featured a nude bodysuit on which a fluffy white tutu gave way to a swan’s head wrapped halter-style around the singer’s neck. She said, “when you're obsessed with something, you can explain it five years later, but in the moment, you don't know exactly why. Right now, swans seem to sort of stand for a lot of things." While everyone from Ellen Degeneres to Kevin James has parodied the dress, it also served as inspiration for a look in the Spring 2014 Valentino show.

Dark eyeliner, tightly braided updo, sheer tank top and full velvet skirt? Doesn’t sound like actress and lifestyle guru Gwyneth Paltrow, but the GOOP founder traded her Cali girl style for a trip to the dark side at the 2002 Oscars. She listed the “goth Alexander Mcqueen” look as one of her biggest fashion mistakes, saying “There were a few issues; I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to – a little bit of punk at the Oscars.”

Uma Thurman’s self-proclaimed “most embarrassing experience”? Selecting this Christian Lacroix dirndl dress for the 2004 awards. The gauzy white confection with its blue and gold waistcoat was more Oktoberfest than Oscars, though the tall blond Kill Bill actress maintained to InStyle that “it was a beautiful dress.” She added, “Turns out I wore it wrong.” The upside is that the look, and Uma, won’t soon be forgotten…