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

It's the starriest night of all.

Oscars dresses

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.

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.

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SEE: Best Oscar Dresses Ever

Jennifer Lopez in Valentino, 20031 of 20
CREDIT: Getty

Jennifer Lopez in Valentino, 2003

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, 19862 of 20
CREDIT: Getty

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, aka 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.'

Barbra Streisand in Arnold Scaasi, 19693 of 20
CREDIT: Getty

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.

Audrey Hepburn in Givenchy, 19544 of 20
CREDIT: Getty

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, 20195 of 20
CREDIT: Getty

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, 20136 of 20
CREDIT: Getty

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. 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, 20067 of 20
CREDIT: Getty

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.

Lupita Nyongu2019o in Prada, 20148 of 20
CREDIT: Getty

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, 20149 of 20
CREDIT: Getty

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.

Angelina Jolie in Marc Bouwer, 200410 of 20
CREDIT: Getty

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.

Beyoncu00e9 in Atelier Versace, 200511 of 20
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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).

Gwyneth Paltrow in Ralph Lauren, 199912 of 20
CREDIT: Getty

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. '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, 200713 of 20
CREDIT: Getty

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.

Zendaya in Valentino Haute Couture, 202114 of 20
CREDIT: Getty

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, 200115 of 20
CREDIT: Getty

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.

Halle Berry in Elie Saab, 200316 of 20
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, 200117 of 20
CREDIT: Getty

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.

Rihanna in Alaïa, 202318 of 20
CREDIT: Imago

Rihanna in Alaïa, 2023

The queen of pregnancy dressing - correction, any dressing - Rihanna knocked it out of the park in 2023, with this polo neck, leather bra and slashed hips situation. 10/10.

Michelle Yeoh in Balenciaga, 202419 of 20
CREDIT: Getty

Michelle Yeoh in Balenciaga, 2024

Sequins can look a little dated on the red carpet, but not in the hands of Michelle Yeoh, who did a masterful take in this one-shouldered gown by Balenciaga.

Celine Dion in John Galliano, 199920 of 20
CREDIT: Getty

Celine Dion in John Galliano, 1999

When Celine Dion arrived at 1999's Oscars, she wasn't just wearing a suit, a backwards suit at that - she was creating a cultural moment in real time. From the double-breasted back that left a triangle of shoulder blade on show to the slanted brim of her fedora, it certainly stood out in the sea of ball gowns - in the best way.

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