Oscar's best-dressed friends: The most memorable fashion winners and losers

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Barbra Streisand 1969

Not only did Barbra Streisand buck the trend for big-entrance dressing by wearing trousers to the Oscars, but also those trousers appeared to be entirely see-through, giving grand guests at the ceremony a none-too-modest glimpse of her derrière as she stepped up to the podium. According to the Los Angeles Times, Arnold Scaasi, designer of the black chiffon two-piece in question, told Streisand: "Let's show people how young and cute you are. Let's forget about that elegant bit." Three years later, Fonda also picked up her award for Klute in trousers – this time a black trouser suit from Rive Gauche, the prêt-à-porter arm of Yves Saint Laurent that had opened four years previously and was taking the world by storm.

Sharon Stone 1996

Rumours raged for weeks over who would dress Sharon Stone for the Oscars in 1996, but here too an unruly streak came to the fore when she appeared in a combination of Valentino and Giorgio Armani (mixing designers is just not done at this particular occasion), and proudly announced that her T-shirt had been plucked from her own wardrobe at the last minute and was from Gap. High Street Fashion on Red Carpet Shock! Unorthodox though this look might be, it was not only elegant but also refreshing and an unusually modern first.

Cher 1988

In the mid-Eighties, the Academy employed Nolan Miller (designer of many a virulently coloured, shoulder-padded jacket for Dynasty) to ensure that actresses toed the line and, instead of wearing anything as radical as, say, a pair of trousers, went back to "looking like stars". In response to this stuffy rule-making, Cher presented the award for best supporting actor at the 58th ceremony in a black sheath by Bob Mackie, topped by a Mohican hairstyle, and quipped: "As you can see, I did receive my Academy booklet on how to dress like a serious actress." In 1988, she picked up the Oscar for best actress, for Moonstruck, in an equally outrageous Mackie creation.

Nicole Kidman 1997

Given her physique, it's not surprising that the world's top designers have long wooed Ms Kidman over her choice of dress on the red carpet in general, and the Oscars in particular. With the pick of Paris's finest couturiers, then, in 1997 the actress opted for an absinthe-green gown from Galliano's debut couture collection for the house of Christian Dior, which cost mere clients in the region of $30,000 to buy, and that is thought to have marked the return of couture rather than humble ready-to-wear (such things are relative, you see) to the red carpet.

Gwyneth Paltrow 1999

Ah, those were the days. This pretty, pink – if admittedly somewhat roomy – gown by Ralph Lauren suited Gwyneth Paltrow to the ground. Her squeaky-clean, all-American credentials were only underlined by the fact that she blubbed uncontrollably when awarded the best-actress Oscar for Shakespeare in Love, and then collapsed into Steven Spielberg's arms. Now, of course, Paltrow would never be seen in such sweet attire, having seemingly fallen under the influence of a savvy stylist who has decreed that she should, henceforth, play the sex kitten rather than the princess. Yawn.

Julia Roberts 2001

By this point, the relationship that had built up between the world's superstar designers and Hollywood's finest had become rather too obvious for the more forward-thinking celebrity stylist: enter the Pleasingly Obscure Fashion Statement, in the form of Julia Roberts, who was awarded best actress for Erin Brockovich wearing vintage Valentino, if you please. Après Ms Roberts, le déluge: it is now almost commonplace for the more discerning stars to appear in what the rest of us might describe simply as very old second-hand clothes.

Angelina Jolie 2004

La Jolie is surprising for the fact that she rarely flaunts her undeniably spectacular credentials when appearing on the red carpet, or indeed anywhere else. She recently, of course, appeared at the SAG Awards in a back-to-front Max Azria design that was more of blue cassock than scene-stealing gown. This Marc Bouwer white satin gown, worn by the actress to the Oscars in 2004, was the exception that proves the rule. Worthy of Jean Harlow, it served as a reminder to any young pretender that Jolie, then as now, is Probably The Most Beautiful Woman In The World. "Who are you with tonight?" asked one red-carpet hack. "I'm alone," she replied. A better dress for a woman on the razzle has yet to be seen.

Björk 2001

"Björk lays egg at Oscars!" screamed the National Enquirer on the morning after the Icelandic star appeared on the red carpet in this dress, which bore more than a passing resemblance to Rod Hull's Emu. Designed by a then almost unknown London Fashion Week fledgling, Marjan Pejoski, its ornithological credentials were only enhanced by the fact that the aforementioned egg, which, it transpired, was designed by her artist boyfriend Matthew Barney, was stuck to her shoe (Balenciaga, for fashion trainspotters out there).

Kate Winslet 2008

Until her recent makeover, Kate Winslet seemed disinterested in the love affair between fashion's big names and Oscar hopefuls. In days gone by, for example, she appeared in low-profile gowns designed by the likes of Ben de Lisi – all very nice but hardly constitute power dressing. That, of course, is the case no longer. She has recently been the poster-girl for everyone from Yves Saint Laurent to Narciso Rodriguez. This pale pistachio goddess-gown marked the start of any new-found fashion credibility. It was designed by Valentino and was a potent symbol of the girl from Reading's rise to Hollywood superstardom.

Cate Blanchett 2007

Question: is it seemly for an actress to dress for the Oscars like a doppelgänger for the trophy itself? Answer: who cares about minor rules of etiquette when they're this impressively thin! And, of course, there's the fact that Blanchett was up for not one but two awards: best actress in Elizabeth: The Golden Age, and best supporting actress for her portrayal of Bob Dylan in I'm Not There. Sadly, she won neither. The dress in question was designed by Giorgio Armani for his exclusive Armani Privé collection. Since this designer dressed Richard Gere in American Gigolo as far back as 1979, he has long demonstrated an understanding of the power of the relationship between fashion and film. Most recently, he dressed Angelina Jolie in black and yellow – like a bumblebee! – for this year's Baftas.

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