The Best Oscars Dresses Of All Time, From Audrey Hepburn to Halle Berry

A feast for the eyes.

Gwyneth Paltrow, Halle Berry, Michelle Williams and Julia Roberts

by Charlotte Pavitt |
Updated on

There is no starrier night than the Oscars. And in preparation for this Sunday, what better excuse for a look back at the most memorable dresses of all time?

From the fairytale - Jennifer Lawrence in a pale pink puffball by Dior - to the formidably fashion forward - Zendaya's sunshine-shaded gown courtesy of Valentino - everyone pulls out all the stops for the Academy Awards (and, naturally, the biggest after party of the year hosted by Vanity Fair).

Ahead of Sunday, we've had a look back at the best dresses from years past. So without further ado, here are some of the most memorable sartorial moments in the history of the Oscars. From Audrey Hepburn's classic outing in Givenchy Couture, back in 1954, to Halle Berry - and, yes, even Bjork.

Gallery

SEE: Best Oscar Dresses Ever

Lauren Hutton, 20061 of 39
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Lauren Hutton, 2006

You don't have to wear a dress to get on the best dressed list. For 2006's red carpet, Lauren Hutton appeared wearing a shrunken tuxedo jacket and cigarette pants that blew all the frothy frocks out of the water.

Jennifer Lopez in Valentino, 20032 of 39
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Jennifer Lopez in Valentino, 2003

Bennifer is back on the table - and this one-shouldered vintage gown from Valentino, which she wore with frosted green eyeshadow, is still one of our all-time favourites from Jennifer Lopez.

Cher in Bob Mackie, 19863 of 39
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Cher in Bob Mackie, 1986

According to Cher, her boyfriend at the time almost passed out when she walked out of her bedroom wearing this showgirl outfit by Bob Mackie. She also said, in a video interview with Vogue, that she wanted to wear it because the powers that be, the Academy, didn't like her. 'They hated the way I dressed, and I had young boyfriends, and they just thought I wasn't serious so I came out and said as you can see I got my handbook on how to dress like a serious actress.'

Cynthia Erivo in Pablo Sebastian, 20174 of 39
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Cynthia Erivo in Pablo Sebastian, 2017

Cynthia Erivo's proved herself to be our favourite red carpet risk-taker in recent years, and this oh-so-elegant little black dress with a difference was the best look in 2017.

Barbra Streisand in Arnold Scaasi, 19695 of 39
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Barbra Streisand in Arnold Scaasi, 1969

Apparently Barbra Streisand didn't realise that her winning look, a spangled suit by Arnold Scaasi, was almost entirely see-through. And while it might not have won best dressed plaudits on the night, it has undoubtedly made it into the most memorable outfits hall of fame.

Viola Davis in Michael Kors, 20186 of 39
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Viola Davis in Michael Kors, 2018

Viola Davis sizzled in the hottest of hot pinks at 2018's Oscars.

Lisa Bonet in Fendi, 20197 of 39
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Lisa Bonet in Fendi, 2019

Lisa Bonet always serves up red-carpet gold, and managed to maintain her laid-back cool even while wearing this sequin-encrusted gown from Fendi.

Octavia Spencer in Christian Siriano, 20198 of 39
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Octavia Spencer in Christian Siriano, 2019

Octavia Spencer had a swoon-worthy moment at 2019's Oscars, wearing off-the-shoulder and full-skirted Christian Siriano.

Constance Wu in Versace, 20199 of 39
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Constance Wu in Versace, 2019

Constance Wu, high off the fashion endorphins from Crazy Rich Asians, came out swinging in sunshine yellow Versace.

Margot Robbie in Chanel, 201810 of 39
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Margot Robbie in Chanel, 2018

My personal favourite (and not just because it's an oh-so bridal look from Chanel) - Margot Robbie at the 2018 Academy Awards.

Brie Larson in Celine, 201911 of 39
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Brie Larson in Celine, 2019

Only Captain Marvel could wear skin-tight chainmail (by Celine, no less) and look this sensational.

Saoirse Ronan in Calvin Klein, 201812 of 39
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Saoirse Ronan in Calvin Klein, 2018

Saoirse Ronan in this satin pink Calvin Klein, complete with bow back, was the epitome of pared-back elegance. Teaching us a lesson in less is more, she teamed her statement dress with a blunt bob and minimal make-up. We, ahem, bow down to you, Miss Ronan.

Audrey Hepburn in Givenchy, 195413 of 39
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Audrey Hepburn in Givenchy, 1954

This belted dress with a subtly floral print and classically full skirt didn't just prove lucky for Hepburn, who went on to receive a statuette for her 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.

Billy Porter in Christian Siriano, 201914 of 39
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Billy Porter in Christian Siriano, 2019

Wearing a fabulous take on the traditional tuxedo, Billy Porter wowed in Christian Siriano at the 2019 Academy Awards.

Jennifer Lawrence in Dior, 201315 of 39
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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 swoon up the stairs. A dramatic pale pink confection by Raf Simons that closed Dior's Haute 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.)

Michelle Williams in Vera Wang, 200616 of 39
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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 gown from Vera Wang, 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 Williams's swept up hair and bright red lips, this is modern Hollywood glamour at its best.

Mila Kunis in Elie Saab, 201117 of 39
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Mila Kunis in Elie Saab, 2011

Mila Kunis is yet another star who has chosen Lebanese couturier Elie Saab to dress them for the biggest night in the Hollywood calendar. For the 2011 Academy Awards, she chose this romantic lilac gown with a draped, almost Grecian-style plunging neckline and a tiered skirt fashioned from strips of lace.

Lupita Nyongu2019o in Prada, 201418 of 39
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Lupita Nyong’o in Prada, 2014

Winning Best Supporting Actress for 12 Years A Slave, Nyong'o wore a custom-made Prada design in a pale blue shade that reminded her of her home city, Nairobi.

Cate Blanchett in Armani Privu00e9, 201419 of 39
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Cate Blanchett in Armani Privé, 2014

Many of Cate Blanchett's most memorable red carpet fashion moments have come courtesy of Mr Armani, and this is arguably one of – if not the - best. For the 2014 ceremony, which saw Blanchett 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.

Amy Adams in Oscar de la Renta, 201320 of 39
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Amy Adams in Oscar de la Renta, 2013

Amy Adams worked in close collaboration with the late design legend Oscar de la Renta for her 2013 Academy Awards gown. The actress, who was nominated for her role in The Master, presented de la Renta with a selection of old black-and-white photos, before one in particular (a picture of a model walking into a doorway, her stylist Cristina Ehrlich told People) captured both their imaginations. The result was this ice blue beaded confection with a tiered tulle skirt.

Angelina Jolie in Marc Bouwer, 200421 of 39
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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 21st century.

Marion Cotillard in Jean Paul Gaultier, 200822 of 39
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Marion Cotillard in Jean Paul Gaultier, 2008

Marion Cotillard took to her first Oscars red carpet like a fish to water (and yes, we are playing on the fact that her idiosyncratically beautiful Jean Paul Gaultier gown was covered in hundreds of mermaid-esque scales). She went on to pick up the Best Actress statuette for her portrayal of Edith Piaf in La Vie En Rose: not bad for a first-timer.

Beyoncu00e9 in Atelier Versace, 200523 of 39
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Beyoncé in Atelier Versace, 2005

For her Academy Awards debut in 2005 (promoting Dreamgirls), Beyoncé chose a vintage strapless gown in black velvet by Atelier Versace. She paired the simple dress with some serious hardware: chandelier earrings and a diamond bracelet by A-list jeweller Lorraine Schwartz (who also designed Bey's 18-carat diamond engagement ring).

Freida Pinto in John Galliano, 200924 of 39
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Freida Pinto in John Galliano, 2009

Freida Pinto's sapphire-blue dress, worn for her post-Slumdog Millionaire appearance at the 2009 ceremony, made its debut on the John Galliano catwalk just a few weeks prior to her red carpet moment. The actor wore the originally risqué (i.e. entirely transparent) style layered over a blue under-dress, a switch-up which allowed the intricate embellishment to do the talking.

Emma Stone in Elie Saab, 201525 of 39
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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.

Gwyneth Paltrow in Ralph Lauren, 199926 of 39
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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 backtracking with 'I don't know if I'd let her chop that one up.'

Penelope Cruz in Versace, 200727 of 39
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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.

Hilary Swank in Guy Laroche, 200528 of 39
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Hilary Swank in Guy Laroche, 2005

To collect her Best Actress Oscar for Million Dollar Baby in 2005, Hilary Swank opted for this deceptively simple gown by French designer Guy Laroche. With its long sleeves and high neckline, the navy-blue gown (fashioned from 27 yards of silk jersey) appeared sedate, even demure, from the front; the cut-away back and exquisite draping, however, made this dress unforgettable. Another lesson in 'less is more' style.

Elizabeth Taylor in Helen Rose, 195729 of 39
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Elizabeth Taylor in Helen Rose, 1957

Elizabeth Taylor certainly knew how to make a statement, as exemplified by her casually pairing this simple draped gown (by MGM costumier Helen Rose, who designed Taylor's outfits for Cat on a Hot Tin Roof, as well as Grace Kelly's now-iconic wedding dress) with a fur stole, elbow-length gloves and a Cartier tiara, a gift from third husband Mike Todd. If ever an image could encapsulate Hollywood glamour, this might just be it.

Jennifer Lopez in Elie Saab, 201530 of 39
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Jennifer Lopez in Elie Saab, 2015

Jennifer Lopez appeared to have danced straight out of a Disney fairytale in this embellished princess dress by red carpet fail-safe Elie Saab. A departure from her typical fashion formula, the couture gown's embellished overlay was decked out in pearls and sequins, while the extensive tulle train was a certified show-stopper.

Cindy Crawford in Versace, 199131 of 39
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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, the designer of choice for the supermodels. The plunging V-neck style wouldn't look out of place on the red carpet today.

Zendaya in Valentino Haute Couture, 202132 of 39
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Zendaya in Valentino Haute Couture, 2021

Kapow! After a year of digital ceremonies, Zendaya wowed and then some on the red carpet at 2021's Oscars, arriving in sunshine-shaded Valentino Haute Couture.

Bjork in Marjan Pejoski, 200133 of 39
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Bjork in Marjan Pejoski, 2001

The picture that sparked a thousand articles, debates and memes (a Debenhams poll published in The Daily Telegraph in 2008 voted it the ninth most iconic red-carpet dress of all time). Perhaps not the most 'fashion' in the traditional sense, but certainly the most memorable.

Gemma Chan in Valentino Haute Couture, 201934 of 39
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Gemma Chan in Valentino Haute Couture, 2019

Styled by the queen of red carpet dressing, Rebecca Corbin-Murray, Chan wore this billowing Valentino Haute Couture gown in 2019 and, to be honest, we're still dreaming about it now.

Grace Kelly in Edith Head, 195535 of 39
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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.

Reese Witherspoon in Dior, 200636 of 39
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Reese Witherspoon in Dior, 2006

This vintage Dior gown dates from the '50s; 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 actor 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-shaped neckline couldn't look better.

Halle Berry in Elie Saab, 200337 of 39
CREDIT: Getty

Halle Berry in Elie Saab, 2003

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

Julia Roberts in Valentino, 200138 of 39
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Julia Roberts in Valentino, 2001

The 2001 Academy Awards was one of the biggest nights in Julia Roberts's 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 Roberts's Oscar moment.

Ruth Negga in Valentino, 201739 of 39
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Ruth Negga in Valentino, 2017

Ruth Negga's bold red Valentino gown is at once subtle and statement-making, and confirmed her status as an exciting new red carpet star back in 2017. It's all in the details: the high neckline, the lace panel detail on the dramatic full skirt, the slightly capped sleeves and the almost empire-line waist, not forgetting the unmissable sky blue of her ACLU pin.

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