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Top 20 Best Oscars Fashion Moments Of All Time

The Academy Awards popularly known as the Oscars ceremony has been an integral awards in the world of cinema. After a year of campaigning for films, taking them to various film festival circuits, and getting recognized at other ceremonies, the last pit stop is the Oscars ceremony. The decorated awards ceremony has been celebrated and marred over the years due to various history-making moments. These moments also include several fashion statements.

During the Oscars, the actors bring their best fashion to the most celebrated event in Cinema. Over the years, now almost a century, the Academy Awards has witnessed some pivotal moments in fashion. In contemporary times, some stylists pick the right fit for the actors. However, the predecessors have been doing that job for themselves creating some indelible fashion moments. The fashion pieces, sometimes, do not merely represent the glamor, but they may be an act of defiance like the Billy Porter iconic tuxedo skirt during the 2019 ceremony. Let’s go down memory lane to pick some of the best fashion moments at the Oscars.

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20) Björk

Björk
Björk

When Björk first strutted the red carpet at the 2001 Oscars event, the tabloids and people both ridiculed the choice of the dress. The awards ceremony has been traditionally inundated with tuxedos and gowns. But, Björk, at the cusp of the new millennium, decided to revolt against the normal and wore this Marjan Pejoski-designed beautiful swan outfit which, once ridiculed, was exhibited at the Metropolitan Museum of Arts during the 2019’s ‘Notes on Camp’ exhibit.

19) Lady Gaga

Lady Gaga during the 2019 Oscars ceremony
Lady Gaga during the 2019 Oscars ceremony

The Bradley Cooper and Lady Gaga starrer ‘A Star Is Born’ created quite a buzz in 2019 due to the infectious chemistry between the two. Gaga also rendered her vocals for some of the most beautiful ballads that year including ‘Always Remember Us’. During the 91st Academy Awards, Lady Gaga, like always, did not leave us unimpressed with a black Alexander McQueen gown wearing the most precious Tiffany & Co., piece of jewelry. In 2019, Lady Gaga won an award for ‘Shallow’.

18) Barbara Streisand

Barbara Streisand
Barbara Streisand

The Oscars ceremony was first televised in 1969. The 41st Academy Awards event did not have a host. It was the year when Barbara Streisand and Katharine Hepburn shared the trophy in the ‘Best Actress’ category. However, the biggest moment during the awards show was Barbara’s shimmery, nude dress. She wore a pajama pantsuit designed by Arnold Scassi. It had a white collar and cuffs and a black satin bow hanging at the neckline with black, sheer bell bottoms.

17) Julia Roberts

Julia Roberts
Julia Roberts

The rom-com extraordinaire, Julia Roberts stunned in a black Valentino vintage gown at the 2001 Oscars ceremony. Originally, the supermodel Helena Christensen wore the gown for the 1992 Valentino couture collection. Roberts donned the velvet-satin gown with a fishtail train with white satin piping starting from her V-neckline and spreading across the dress. The actress wore Van Cleef and Arpels jewelry. Julia won the award for ‘Erin Brockovich’ in the ‘Best Actress’ category.

16) Halle Berry

Halle Berry
Halle Berry

Halle Berry exudes inexplicable style and beauty. Nothing was different during the 2002 Oscars ceremony! She wore one of the most iconic dresses during the most iconic edition of the Academy Awards. The actress wore an Elie Saab semi-sheer gown. It had floral appliqués covering the bodice with an asymmetrical taffeta skirt. In 2002, Berry became the first Black Actress to take home the golden statuette.

15) Gwyneth Paltrow

Gwyneth Paltrow
Gwyneth Paltrow

If there is one dress that divided the fashion police in the history of the Oscars is Gwyneth Paltrow‘s gown during the 1999 ceremony. At the 71st Academy Awards ceremony, Gwyneth Paltrow looked ethereal in a bubblegum pink Ralph Lauren dress. The pink taffeta gown had spaghetti straps with a V-neckline and a full skirt with tulle wrapped around her hands. In 1999, she won an Oscar for ‘Shakespeare in Love’.

14) Faye Dunaway

The iconic Faye Dunaway outfit
The iconic Faye Dunaway outfit

In 1968, Faye Dunaway turned heads with her long-sleeved chiffon dress with a feather coat. The look was created by Theodora Van Runkle. During that night, she was nominated for an Oscar for ‘Bonnie and Clyde’.

13) Audrey Hepburn

Audrey Hepburn
Audrey Hepburn

The year 1954 was an important year for the actress and fashion icon Audrey Hepburn. In 1954, she got her first Oscar nomination for ‘Roman Holiday’. Also, it was the year when she, for the first time, wore a Givenchy dress, the brand which defined the icon she is today! At the event, she wore a floral patterned dress with a petite belt with a boat neck.

12) Zendaya

Zendaya in Valentino
Zendaya in Valentino

If we can attribute Zendaya’s fashion to an animal, a chameleon would be perfect to describe her red carpet looks. The actress dresses for the occasion. During most of the film promotions, she wore a theme-accurate dress. So, at the most decorated awards ceremony, the ‘Dune’ actress bedazzled in a Valentino Haute Couture. During the 2022 fateful Oscars ceremony, she wore a crop shirt with a silver, sequin embroidered skirt with Bulgari Serpenti Viper bangles.

11) Gemma Chan

Gemma Chan
Gemma Chan

Gemma Chan’s dress during the 2019 Oscars ceremony was the epitome of couture meets comfort! During the ceremony, she wore a pink, ruffled statement Valentino gown. It had a high, ruffled collar with utility pockets by the genius Pierpaolo Piccoli.

10) Sharon Stone

Sharon Stone at the Oscars wearing Gap and Vera Wang
Sharon Stone at the Oscars wearing Gap and Vera Wang

Sharon Stone walked, so Zendaya could run! During the 1998 ceremony, Stone ditched the usual, traditional gown. On the red carpet, she appeared in a Gap buttoned-down crisp white shirt and a purple Vera Wang skirt. Daya also went for the same look at the 2022 event.

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9) Salma Hayek

Salma Hayek in Armani
Salma Hayek in Armani

Salma Hayek was the new girl on the Mexican girl on block! In 1997, she was presenting at the awards ceremony for the first time. So, she was dressed for the event without knowing that her look will become an iconic one in the Oscars’ fashion archives. She wore a Giorgio Armani slip dress with a statement tiara piece.

8) Elsie Fisher

Elsie Fisher
Elsie Fisher

When it is someone’s debut at one of the most revered awards events, the pressure is off the top about how to look. But, Elsie Fisher is an exception who looked effortless channeling the androgynous self in fashion! In 2019, Fisher wore a three-piece suit designed by Thom Browne with a silver collar clip.

7) Jennifer Lawrence

Jennifer Lawrence
Jennifer Lawrence

During the 65th Academy Awards ceremony, Jennifer Lawrence won the ‘Best Actress’ award for the Bradley Cooper starrer ‘Silver Linings Playbook’. Lawrence reportedly wore the most expensive dress in the history of the Oscars. She wore a Christian Dior strapless, pink, voluminous dress from their Haute Couture collection. The dress was worth $4 million, and it was one of the most exquisite pieces.

6) Lauren Hutton

Lauren Hutton
Lauren Hutton

Lauren Hutton wore one of the most iconic outfits during the Oscars 1975. The supermodel wore a rainbow Halston gown with a fur coat with it. Street style meets elegance.

5) Angelina Jolie

Angelina Jolie
Angelina Jolie

The undisputed queen of the Oscars red carpet is Angelina Jolie. On several occasions, she has served some of the most iconic red carpet-looks in history. However, the 2004 Marc Bouwer dress was the most loved Oscars look of all time. In March 2023, the British marketplace OnBuy surveyed their favorite outfits from the Oscars red carpet. 3,000 people participated in it and they unanimously picked this satin, white slip dress halter neck.

4) Emma Stone

Emma Stone
Emma Stone

During the fateful 2017 Oscars ceremony, Emma Stone gave us old Hollywood with her Givenchy Haute Couture dress. Stone won the award for ‘La La Land’ in ‘Best Actress in a Leading Role’. The dress comprised laces, beading, and fringe. It took 1,700 hours at the Givenchy Atelier to create the dress.

3) Natalie Portman

Natalie Portman
Natalie Portman

During the 92nd Academy Awards ceremony, Natalie Portman made a historic fashion statement with her Dior Haute Couture dress. She wore a black dress with a sheer neckline and gold embroidery and a statement cape. The cape had names of the female directors who were snubbed by the Academy during the ceremony.

2) Billy Porter

Billy Porter in a tuxedo gown
Billy Porter in a tuxedo gown

One of the most iconic male looks at the Oscars was that of Billy Porter who wore a Christian Siriano tuxedo gown at the Academy Awards 2019.

1) Prince

Prince
Prince

During the 57th Academy Awards, Prince wore a purple, sequinned jumpsuit with a veil. That night, he won the award for ‘Best Original Song Score’. He was the icon and one of the trailblazers when it comes to androgynous fashion.

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Nishant Bhise
Nishant Bhisehttps://firstcuriosity.com/
Nishant Bhise is a Sub-Editor at FirstCuriosity. He has more than 2 years of experience in Entertainment content writing with the organization. Besides being a journalist and humanist, he loves cinema and intersectionality, basically everything that screams love, hope, and of course, Lady Gaga. Nishant loves and breathes popular culture, music, especially hip-hop and pop, and the royal family drama. Along with that, he takes great interest in the happenings in the technology world and politics. He is an LGBTQIA+ ally. Approach him with an apple juice to discuss Modern Family, Pose, and Schitt’s Creek.

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