Actress Audrey Hepburn at the 26th Academy Awards (Photo: Archive Photos/Getty Images)
Cover Actress Audrey Hepburn poses with her trophy at the 1954 Oscars (Photo: Archive Photos/Getty Images)
Actress Audrey Hepburn at the 26th Academy Awards (Photo: Archive Photos/Getty Images)

Here's a rundown on “who wore what” at the Oscars over the years

Since its first iteration as a private dinner in 1929, the Academy Awards has grown exponentially in scale and status. It’s a gathering of the who’s-who of the Hollywood elite, synonymous with a parade of black ties and ritzy ball gowns.

Also known as the Oscars and often dubbed “Hollywood’s biggest night”, the Academy Awards is a platform for celebrities to showcase their finest style capabilities. The ceremony has witnessed some of entertainment history’s most notable fashion moments. Millions around the world tune in to watch its live broadcast each year and continue to be enthralled by the glitz and the glamour.

Let’s revisit the memorable looks that graced the presence of the golden statuette.

More from Tatler: Blast from the past: the best Oscars looks during Hollywood's golden years

Audrey Hepburn, 1954

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Audrey Hepburn at the Academy Awards Ceremonies (Photo: Getty Images)
Above Audrey Hepburn at the Academy Awards Ceremonies (Photo: Getty Images)
Audrey Hepburn at the Academy Awards Ceremonies (Photo: Getty Images)

A 24-year-old Audrey Hepburn won the Best Actress award for her captivating performance as Princess Ann in Roman Holiday. The young actress wore a white floral Givenchy dress to the 26th Academy Awards. The dress cinched at the waist and had a boat neckline, which people considered unusual to wear to the Oscars during those days.

 

Barbra Streisand, 1969

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Barbra Streisand (Photo: Ron Galella/Ron Galella Collection via Getty Images)
Above Barbra Streisand (Photo: Ron Galella/Ron Galella Collection via Getty Images)
Barbra Streisand (Photo: Ron Galella/Ron Galella Collection via Getty Images)

Barbra Streisand wore a black pantsuit by Arnold Scaasi to the 41st Academy Awards, during which she and Katharine Hepburn had tied for the Best Actress award. The ensemble featured flared legs, tuxedo cuffs, and a large black bowtie. In a slight blunder, the outfit turned sheer under the bright lights, a moment Streisand recalls with amusement.

 

Cher, 1973

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Sonny Bono and Cher (Photo: Ron Galella/Ron Galella Collection via Getty Images)
Above Sonny Bono and Cher (Photo: Ron Galella/Ron Galella Collection via Getty Images)
Sonny Bono and Cher (Photo: Ron Galella/Ron Galella Collection via Getty Images)

Cher showed up to the 45th Academy Awards in a gold two-piece number designed by Bob Mackie. The singer wore a jewel-encrusted outfit that showed off her bare midriff and flattered her slender figure. She wore her long black hair down and loose, matching it with gold hoop earrings and sharp pink nails.

Salma Hayek, 1997

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Salma Hayek (Photo: Jim Smeal/Ron Galella Collection via Getty Images)
Above Salma Hayek (Photo: Jim Smeal/Ron Galella Collection via Getty Images)
Salma Hayek (Photo: Jim Smeal/Ron Galella Collection via Getty Images)

At the 69th Academy Awards, Salma Hayek looked like absolute royalty in a crystal-embellished pink Armani slip dress. The then-rising actress accessorised her updo with a tiara, along with silver sandals and a matching satin handbag. She completed the look with shimmery green eyeshadow.

See also: Historic firsts at the Oscars 2025

Gwyneth Paltrow, 1999

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Gwyneth Paltrow during 1999 Vanity Fair Oscar Party (Photo: Barry King/WireImage)
Above Gwyneth Paltrow during 1999 Vanity Fair Oscar Party (Photo: Barry King/WireImage)
Gwyneth Paltrow during 1999 Vanity Fair Oscar Party (Photo: Barry King/WireImage)

Though this Ralph Lauren look received mixed reviews at the time, Gwyneth Paltrow’s appearance at the 71st Academy Awards was credited with reviving pink in the fashion world. The actress, who took home the Best Actress award for her role in Shakespeare in Love, paired the look with matching pink Manolo Blahnik sandals and jewellery from Harry Winston.

Halle Berry, 2002

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Halle Berry poses with her  Actress in a Leading Role Oscar for "Monster's Ball" (Photo: Steve Granitz/WireImage)
Above Halle Berry poses with her Actress in a Leading Role Oscar for "Monster's Ball" (Photo: Steve Granitz/WireImage)
Halle Berry poses with her  Actress in a Leading Role Oscar for "Monster's Ball" (Photo: Steve Granitz/WireImage)

Halle Berry made history in this deep-red dress by Elie Saab when she became the first African-American woman to win the award for Best Actress at the 74th Academy Awards. The semi-sheer ensemble consisted of an asymmetrical taffeta skirt and a mesh bodice embroidered with floral appliqués. In March 2023, the Academy Museum displayed the said dress.

Read more: The people who made Oscars history: Michelle Yeoh, Hattie McDaniel, and more

Lupita Nyong'o, 2014

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Lupita Nyong'o arrives at the 86th Annual Academy Awards (Photo: Axelle/Bauer-Griffin/FilmMagic)
Above Lupita Nyong'o arrives at the 86th Annual Academy Awards (Photo: Getty Images)
Lupita Nyong'o arrives at the 86th Annual Academy Awards (Photo: Axelle/Bauer-Griffin/FilmMagic)

Lupita Nyong’o looked like she stepped out of a fairy tale in a custom-designed powder blue gown by Prada, which she wore to the 86th Academy Awards. The powder blue silk number featured a plunging neckline and a flowing pleated skirt with beaded embellishments designed to resemble champagne bubbles. Nyong’o won the Best Supporting Actress award for her performance in 12 Years a Slave.

Gemma Chan, 2019

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Gemma Chan attends the 91st Annual Academy Awards (Photo: Frazer Harrison/Getty Images)
Above Gemma Chan attends the 91st Annual Academy Awards (Photo: Frazer Harrison/Getty Images)
Gemma Chan attends the 91st Annual Academy Awards (Photo: Frazer Harrison/Getty Images)

Gemma Chan made a dramatic statement at the 91st Academy Awards, decked out in a voluminous pink, pleated taffeta dress by Valentino. The floor-length gown featured a ruffled high collar and pockets. The Crazy Rich Asians star also wore a rhinestone hairpin and jewellery from Bulgari.

Michelle Yeoh, 2023

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Michelle Yeoh attends the 91st Annual Academy Awards (Photo: Frazer Harrison/Getty Images)
Above Michelle Yeoh attends the 91st Annual Academy Awards (Photo: Frazer Harrison/Getty Images)
Michelle Yeoh attends the 91st Annual Academy Awards (Photo: Frazer Harrison/Getty Images)

In another history-making turn of events, Michelle Yeoh brought home the Best Actress award, becoming the first woman of Asian descent to win the prize. She wore a Dior haute couture gown designed exclusively for her by Maria Grazia Chiuri. It consisted of ivory silk organza bedecked with white feathers. The resulting look was nothing short of heavenly.

 

Zendaya, 2024

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Zendaya attends the 96th Annual Academy Awards (Photo: Getty Images)
Above Zendaya attends the 96th Annual Academy Awards (Photo: Getty Images)
Zendaya attends the 96th Annual Academy Awards (Photo: Getty Images)

The always-stylish Zendaya is no stranger to heads constantly turning in her direction and her stylist, Law Roach, made sure all eyes were on the starlet as she graced the 2024 Oscars red carpet. She channelled Old Hollywood glamour in a silk pink and gunmetal Armani Privé dress, paired with pink gold high jewellery pieces from Bulgari including a bracelet, ring, and earrings.

 

Ariana Grande, 2025

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Ariana Grande attends the 97th Annual Oscars (Photo: Chelsea Guglielmino/FilmMagic via Getty Images)
Above Ariana Grande attends the 97th Annual Oscars (Photo: Chelsea Guglielmino/FilmMagic via Getty Images)
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HOLLYWOOD, CALIFORNIA - MARCH 02: Ariana Grande performs onstage during the 97th Annual Oscars at Dolby Theatre on March 02, 2025 in Hollywood, California.  (Photo by Kevin Winter/Getty Images)
Above Ariana Grande performs onstage during the 97th Annual Oscars (Photo: Kevin Winter/Getty Images)
Ariana Grande attends the 97th Annual Oscars (Photo: Chelsea Guglielmino/FilmMagic via Getty Images)
HOLLYWOOD, CALIFORNIA - MARCH 02: Ariana Grande performs onstage during the 97th Annual Oscars at Dolby Theatre on March 02, 2025 in Hollywood, California.  (Photo by Kevin Winter/Getty Images)

First-time Oscar nominee for Best Supporting Actress Ariana Grande pulled up to the Dolby Theatre in not one, but two custom Schiaparelli creations. Her first look consisted of a blush pink bustier dress with a peplum waist—a nod to her role as Glinda the Good. She changed into a strapless ruby slipper-red sequin gown and matching shoes for her “Defying Gravity” duet with co-star Cynthia Erivo. Though she didn’t end up winning the award, she clearly had two of the most popular looks of the night.

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Julianna Cabili
Features Writer, Tatler Philippines
Tatler Asia

About

Julianna has been interested in leading a literary life since she first read Frances Hodgson Burnett's A Little Princess at eight. Before working with Tatler, she was an archive intern at The Center for Fiction in Brooklyn, New York. She is a textbook Pisces who devotes most of her spare time to her crochet projects, watching classic films, and going through her never-ending pile of unread books. She studied creative writing, global literature and art history at Sarah Lawrence College, graduating with a Bachelor of Arts degree in 2022. Toni Morrison, Nora Ephron, Clarice Lispector and Jia Tolentino are among her all-time favourite writers.

Work

Julianna writes about fashion, beauty, sustainability, and the arts. She is always keen on conducting interviews with talented women who are changing the game in their respective fields. 

For event invites and story leads, hit her up at julianna.cabili@tatlerasia.com