Red Carpet

The Best Oscars Dresses Of All Time

There is no bigger night in the Hollywood calendar than the Oscars, with all eyes on the red carpet as the film industry's brightest stars vie to be crowned best dressed.

Ahead of the 89th Academy Awards on Sunday evening, here are some of the most memorable sartorial moments in Oscars history, from Audrey Hepburn's classically chic outing in Givenchy couture to Emma Stone dazzling in Elie Saab...

Audrey Hepburn in Givenchy, 1954

This belted dress with a subtly floral print and classically Fifties full skirt didn’t just prove lucky for Hepburn, who went on to receive the Best Actress statuette for her winning turn in Roman Holiday. The ceremony also marked the first time she wore a Hubert de Givenchy design to a Hollywood event. The designer had dressed her for Sabrina the previous year, marking the start of a sartorial partnership that would see Hepburn write Givenchy into her future film contracts. ‘His are the only clothes in which I am myself,’ she remarked in 1956.

Angelina Jolie in Marc Bouwer, 2004

The thigh-high split of her black Atelier Versace gown may have launched a thousand memes when Angie attended the Oscars ceremony in 2012, but it’s her 2004 dress that is arguably her best: a white satin gown by South African designer Marc Bouwer that immediately recalls the infamous halter neck style worn by Marilyn Monroe in The Seven Year Itch, bringing old Hollywood glamour into the twenty-first century.

Grace Kelly in Edith Head, 1955

It’s hard to imagine any of this year’s Oscar contenders re-wearing a gown for their big night, however beloved. Grace Kelly, however, wore this pale blue-green gown, designed by costumier extraordinaire Edith Head, for the New York premiere of The Country Girl the previous year, choosing to recycle it when that film earned her an Academy Award nomination (and eventually, a win). She would go on to wear it a third time on the cover of Life magazine a few weeks later. Sixty years later, it remains one of her most iconic looks.

Cate Blanchett in Armani Privé, 2014

Many of Cate Blanchett’s most memorable red carpet fashion moments have come courtesy of an Armani showstopper, and this is arguably one of – if not the - best. For the 2014 ceremony, which saw Cate take home the Best Actress statuette for Blue Jasmine, her ensemble was worth an estimated $18.1 million: $100,000 for this stunning embellished gown in pale blush, then a further $18 million for her Chopard earrings, bracelet and ring.

Gwyneth Paltrow in Ralph Lauren, 1999

Gwyneth’s pale pink Ralph Lauren gown, with its spaghetti straps and full, Disney princess skirt, is arguably as famous as the tearful acceptance speech she made after winning Best Actress for Shakespeare In Love. The actress later revealed that she’s kept all of her Oscar gowns for her daughter Apple, and hopes she’ll wear the pink gown to her prom. ‘Maybe she’ll wear it to prom and do a Pretty in Pink thing and resew it and cut it up,’ she mused to People, before checking that idea with ‘I don’t know if I’d let her chop that one up.’

Penelope Cruz in Versace, 2007

She may have lost out to Queen Helen Mirren in the race to the Best Actress trophy at the 79th Academy Awards, but Penelope Cruz was a winner on the red carpet in this sweeping blush-coloured number. While pale pink princess gowns are a mainstay of classic Oscars style (see Gwyneth Paltrow, Jennifer Lawrence et al), the feathered skirt and sculptural bodice make this Atelier Versace number a showstopper in its own right.

Michelle Williams in Vera Wang, 2006

An old style adage decrees that blondes shouldn’t wear yellow. Michelle Williams put paid to that particular rule with her sunshine yellow Vera Wang gown, arguably one of the most instantly memorable Oscars dresses of recent years. From the bold colour to the ruffled shoulder detailing, the draped skirt to Michelle’s swept up hair and bright red lips, this is modern Hollywood glamour at its best.

Jennifer Lawrence in Dior, 2013

‘I think I just stepped on the fabric and they waved the stairs or something. What went through my mind? A bad word that I can’t say.’ J. Law’s 2013 Oscars dress is worthy of your attention, and not just because it precipitated that memorable fall. A dramatic pale pink confection by Raf Simons that closed Dior’s spring/summer couture show in 2013, it proved that Lawrence can pull off Old Hollywood style like no one else (despite her persona being as far from the staid stars of the studio era as possible…)

Lupita Nyong’o in Prada, 2014

It's hard to believe that the 2014 ceremony marked Lupita Nyong'o's first ever Oscars, so assuredly has she cemented her reputation as both a fashion-forward red carpet presence and a major acting talent in the ensuing years. Taking the Best Supporting Actress award for 12 Years A Slave, Lupita wore a custom-made Prada design worthy of a Grecian goddess, in a pale blue shade that reminded her of her home city, Nairobi.

Reese Witherspoon in Dior, 2006

This vintage Dior gown dates from the 1950s; appropriately, that’s the decade Reese returned to for her Oscar winning turn as June Carter-Cash in Walk The Line. Rumour has it that the actress had to fight for this piece of fashion history, which was reportedly originally designed for royalty, after finding it in a Paris boutique. Just like Elle Woods, her perseverance paid off: the intricate beading, muted colours and classic V neckline couldn’t look better.

Emma Stone in Elie Saab, 2015

Emma Stone made it clear that she isn't afraid to take risks on the red carpet when she chose this beaded Elie Saab gown in a statement-making shade of chartreuse (that's fashion speak for 'yellow-green') that works unexpectedly well with her red hair. Judging on past performance, we can't wait to see what she steps out in on Sunday as the favourite to win Best Actress for La La Land.

Farrah Fawcett in Stephen Burrows, 1978

With her dramatic curls and aura of Studio 54 glamour, the Charlie's Angels star was the epitome of Seventies disco chic in this gold chainmail slip dress by American designer Stephen Burrows. When in doubt, dress like an Oscar statuette, after all...

Cindy Crawford in Versace, 1991

Attending the Academy Awards in 1991 as one half of the ultimate Nineties power couple (with then-boyfriend Richard Gere), Cindy Crawford managed to steal the show in this simple yet iconic scarlet dress courtesy of Versace, designer of choice for the supermodels. The plunging V-neck style wouldn't look out of place on the red carpet today.

Julia Roberts in Valentino, 2001

The 2001 Academy Awards was one of the biggest nights in Julia Roberts’ career: she was nominated for – and went on to win - Best Actress for her role in Erin Brockovich. To find the perfect dress, she looked back through Valentino’s archives, eventually choosing to keep things simple in this classic black and white style from 1984. Appropriately enough, the designer said he had been inspired by the allure of movie stars when working on the collection nearly twenty years before Julia’s Oscar moment.

Halle Berry in Elie Saab, 2003

Elie Saab gowns have become a mainstay of red carpet style, with Halle Berry amongst the label's legion of famous fans. The actress memorably wore a Saab creation with a sheer bodice when she made history as the first African-American Best Actress winner in 2002, and chose a simpler style by the same designer for the next year's ceremony, wowing in layers of embellished gold tulle.

Look back at more of the most iconic Oscars dresses in Hollywood history in the gallery below...


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