In 1954, Audrey Hepburn was nominated for a best actress Oscar for Roman Holiday and accepted the award in Givenchy. The actor, then 24, would become inextricably linked with the French couturier, each nourishing the other’s career, but it was at the Oscars where their relationship gelled. Hepburn demonstrated her capacity for elegance with Givenchy’s classic white gown, gently cinched at the waist. It engendered a lifelong partnership. She became his muse, he became her costume designer and the pair eventually became business partners Photograph: Bettmann/Corbis
Elizabeth Taylor had style in spades. In the 80s the actor went brash in Valentino, in the 70s it was all boobs and Halston, and in the 60s she was a riot of bling and waist – a look that was at its apogee at the 1961 Oscars when Taylor, then 28, won best actress for Butterfield 8. The success of the dress is threefold: first the printed skirt, which pre-empted Alexander McQueen; then, the sheer top whose impact would have been nothing had she not possessed what Richard Burton coined her “apocalyptic breasts”; and who else would have had the temerity to channel a pan-African flag? Photograph: Darlene Hammond/Getty Images
Behold: a woman wrestling with changing decades. Kim Basinger attended the 1990 Oscars wearing this remarkable number that, part debutante, part Miss Havisham, was altogether weird. Following the success of Batman and 9½ Weeks, the actor, then 37, was at the height of her fame and decided to mark the occasion by customising a relatively prosaic white satin ballgown with personal flourishes. One collar popped, the other halfway down her arm; one shoulder exposed, one arm gloved; the effect finished off with a heavy slick of lipstick. The result? A monstrosity Photograph: Sipa Press/Rex Features
1993 was not an especially upbeat year at the Oscars – The Piano cleaned up, Mrs Doubtfire barely got a look in – so it might have been in a bid to redress the balance that Whoopi Goldberg eschewed the tyranny of black tie to wear a dress, a jumpsuit and a cape in purple and lime green brocade, simultaneously. The look, “inspired” by Disney, almost worked. This was the 90s, after all. And she was Whoopi Goldberg, a decidedly anti-fashion, Oscar-winning actor fronting an eponymous chatshow, one of the highest paid actors in Hollywood and, in her words, “born ham”. Sadly it tanked Photograph: Frank Trapper/Sygma/Corbis
Costume designer Lizzy Gardiner won an Oscar for best costume design in 1995 for Priscilla, Queen of the Desert, and chose to attend in a dress fashioned from 254 expired American Express gold cards. The dress was not designed for the ceremony but was a reject from the film’s wardrobe. Costume designers are, of course, exempt from placating designers. Rather, they are encouraged to showcase their handiwork. Not that this was Gardiner’s only motivation. “I’m broke,” she trilled to the press, “and I didn’t have anything to wear.” Well, nothing screams poverty like AmEx Photograph: Barry King/Getty Images
“A profusion of confusion,” sniped the influential US fashion critic, Mr Blackwell, of Canadian singer Celine Dion’s white tux as worn, oversized and back-to-front, at the 1999 Oscars. Where to begin: the surplus of fabric, the curious decision to finish off the look with a fedora, jauntily tipped, as well as sunglasses? Worse of all, it’s Dior. One doubts whether the label endorsed her decision to wear it backwards but either way, who would do that to the house at which the lady-tux was forged, thus trampling all over its legacy and (let’s face it) modern fashion? Kudos for anticipating the boyfriend blazer by, like, a decade though Photograph: Jim Smeal/WireImage
In Oscar parlance, 2001 was The Year of Gladiator. To everyone else, it was the year Björk went renegade and wore a swan to the Oscars, which then proceeded to spontaneously lay eggs on the red carpet, much to the chagrin of security. The dress designed by Macedonian designer, Marjan Pejoski, invoked mass derision but beak aside, was almost pretty. Almost. Still, that she attended the ceremony at all is miraculous. Nominated for best original song for “I’ve Seen It All” in Lars Von Trier’s Dancer in the Dark, it later emerged that Björk was so unhappy during filming it was rumoured that she ate her own cardigan Photograph: Stewart Cook/Rex Features
Angelina Jolie’s low-key, yellow-darted Armani Privé dress as worn circa The Tourist at the 2009 Baftas was hardly groundbreaking. But neither was it an arbitrary choice. Much like Lenny Henry, the actor tends towards colour when she’s entertaining, darker tones when she’s in Africa, but here wore both – accessorised by excellent hair, excellent ankles and whip-thin arms. It just goes to show that yellow can work if you’re fit enough and that a macrobiotic diet is sometimes worth it. Just look at that face: a mother in the rudest of health, an actor who knows her film sucks too much for floor-length Photograph: Mike Marsland/WireImage
Green was the colour of choice, and exposed shoulders were big at last year’s Golden Globes, but actor Emma Stone, 22, nominated for her role in Easy A, went rogue, opting instead for a flesh-coloured, cap-sleeved backless gown by Calvin Klein as well as a buttery tan. What with the wholesome up-do, it could have been fantastically dull but was in fact one of the only examples of a mainstream trend (nude) being successfully luxed up and exercised on a red carpet. Less a dress, more a fine modern gesture. And because if you looked like Stone you, too, would opt to swan about in what is essentially a bodystocking Photograph: Jason Merritt/Getty Images
Nowadays, scrutinising Helena Bonham Carter’s wardrobe seems a little churlish. She is the only woman to wear Vivienne Westwood as Westwood intended. But that didn’t stop her goosing the haters into action at the 2011 Golden Globes where she represented The King’s Speech in a crumpled Westwood silhouette, mad hair and different coloured shoes. Two years ago Justin Bieber pulled off a similar stunt wearing bi-coloured glasses to promote Never Say Never, and it became the highest grossing concert film to date. Method to the madness? The King’s Speech did pretty well at the box office too Photograph: Jason Merritt/Getty Images
