50 Celebrities Oscars Fashion Through The Years

The fact that Rita Moreno wore the same dress to the Oscars in 1962 and 2018 is AMAZING.

1.

This is what Lupita Nyong’o looked like at the Oscars in 2014, in all of her dreamy Cinderella glory, the night she won Best Supporting Actress for 12 Years a Slave.


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A legit angel in her blue, flowing dress.


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2.

Here’s Cher (alongside Don Ameche) at the 1986 Oscars. She apparently showed up in this extravagant outfit as a presenter because she knew the Academy didn’t take her seriously as an actor.


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Two years later, Cher would win Best Actress for Moonstruck, wearing this very memorable Bob Mackie creation.


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3.

This is how Billy Porter showed up to the 2019 Oscars: In a black tuxedo dress!!! Like, no other man has ever looked this good at the Academy Awards. Not exaggerating.


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Just kidding — another man did look just as good a year later at the 2020 Oscars, and that man was Billy Porter! Here he’s wearing another beautiful dress, only he took a more colorful route. Well done, sir!


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4.

Before there was Cher at the Oscars, there was Barbra Streisand. Pictured in a sparkly, see-through outfit, Streisand won Best Actress for Funny Girl in 1969 (tying that year with Katharine Hepburn for The Lion in Winter).


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Here’s what the back of Streisand’s iconic outfit looked like:


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Streisand would go on to win the Oscar for Best Original Song for A Star Is Born in 1977.

5.

Here’s what Rita Moreno looked like at the Oscars in 1962, alongside her West Side Story co-star George Chakiris. That night, they won for Best Supporting Actress and Best Supporting Actor for their roles in the legendary movie musical.


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Fun fact: Moreno rocked the SAME EXACT DRESS 56 years later at the Oscars in 2018. Talk about an icon!


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6.

This is what the incomparable Halle Berry looked like at the Oscars in 2002, wearing a burgundy, transparent dress with vines and flowers covering the top. That night she won Best Actress for Monster’s Ball (the first Black woman to ever win in this category).


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7.

Here’s what Meryl Streep looked like at the 2012 Oscars, in the goldest of gold gowns, where she won her THIRD Oscar for Best Actress for The Iron Lady.


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Streep won Best Supporting Actress for Kramer vs. Kramer in 1980 and Best Actress for Sophie’s Choice in 1983.

8.

Here’s Diane Keaton, the true queen of fashion, at the 1976 Oscars as a presenter — rocking a white suit, polka dot tie, and striped buttoned-down shirt. A clashing outfit for the ages.


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Keaton would go on to win the Oscar for Best Actress for Annie Hall the following year.

9.

This is what a very happy Spike Lee looked like at the Oscars in 2019, wearing a purple suit to honor the king of purple: Prince. That night, Lee finally won a competitive Oscar for Best Adapted Screenplay for BlacKkKlansman.


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Lee won an Honorary Oscar in 2015.

10.

Here’s what legendary stage and screen actor Cicely Tyson looked like at the Oscars in 1978, presenting an award in a beautiful white gown and golden hairpiece.


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Tyson would go on to receive an Honorary Oscar in 2018.

11.

This is what Björk looked like at the 2001 Oscars, rocking her infamous swan dress. That night she was nominated for Best Original Song for “I’ve Seen It All” from Dancer in the Dark.


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12.

Here’s what Jennifer Lopez and Ben Affleck looked like at the Oscars just a few years later in 2003, during their first original run as Bennifer. Lopez’s beautiful, light green gown would go down as one of her most iconic looks in her career.


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Affleck (along with Matt Damon) won the Oscar for Best Original Screenplay for Good Will Hunting in 1998, and would go on to win Best Picture for Argo in 2013.

13.

Here’s what legendary singer Céline Dion showed up in at the 1999 Oscars: a white backward suit with a matching cowboy hat and silver jewelry. A ’90s icon!

14.

Here’s what legend in her own time Zendaya looked like at the Oscars in 2021, giving a subtle nod to Cher’s signature look from the ’70s. Apparently, this dress glowed in the dark when Zendaya wasn’t showing it off in the sunshine — we love an Oscars look with multiple layers (pun intended).


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15.

This is what the positively stunning Janelle Monáe looked like at the 2017 Oscars, wearing a mystical, see-through, black gown with golden jewelry to top it off. That night, two films she starred in were nominated for Best Picture (Moonlight and Hidden Figures), and the gold statue went to Moonlight.


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Look! At! These! Rings!


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16.

Here’s the iconic Elizabeth Taylor with her then-husband Eddie Fisher (Carrie Fisher’s dad!) at the 1961 Oscars. That night she won Best Actress for Butterfield 8.


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Taylor would go on to win the Oscar for Best Actress for Who’s Afraid of Virginia Woolf? in 1967.

17.

Here’s Diana Ross in a beyond fabulous suit, with a checkered vest and a corsage pinned to her blazer, at the 1973 Oscars. That night she was nominated for Best Actress for Lady Sings the Blues.


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18.

This is what Lady Gaga looked like (in all of her elegant glory) the night she won Best Original Song for “Shallow” from A Star Is Born in 2019. She rocked a very notable yellow diamond necklace that Audrey Hepburn wore in Breakfast at Tiffany’s.


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19.

Here’s Viola Davis, happy as can be, holding up her WELL-DESERVED, supremely overdue Oscar for Best Supporting Actress for Fences in 2017. Fun fact: She invented the color red this very night!


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20.

This is what a 10-year-old Angelina Jolie looked like as a Madonna-esque “Material Girl” at the 1986 Oscars. That night she went with her father, Oscar winner Jon Voight, and in 2000, she’d win a golden statue of her own for Best Supporting Actress for Girl, Interrupted.


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21.

Here’s what Chadwick Boseman with wife Taylor Simone Ledward looked like at the Oscars in 2019:


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22.

Here’s what Angela Bassett looked like at the Oscars in 2000:


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23.

Here’s what Jane Fonda looked like at the Oscars in 1971:


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That night, Fonda won the Oscar for Best Actress for Klute, and would go on to win the Oscar for Best Actress for Coming Home in 1979.

24.

Here’s what Jack Nicholson and Anjelica Huston looked like at the Oscars in 1975:


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Nicholson would go on to win the Oscar for Best Actor for One Flew Over the Cuckoo’s Nest in 1976, Best Supporting Actor for Terms of Endearment in 1984, and Best Actor for As Good as It Gets in 1998.

Huston would go on to win the Oscar for Best Actress for Prizzi’s Honor in 1986 (which was directed by her father, Hollywood legend John Huston).

25.

Here’s what Kate Winslet looked like at the Oscars in 1996:


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Winslet would go on to win the Oscar for Best Actress for The Reader in 2009.

26.

Here’s what Will Smith and Jada Pinkett Smith looked like at the Oscars in 1997:


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27.

Here’s what Demi Moore looked like at the Oscars in 1989:

28.

Here’s what Penélope Cruz looked like at the Oscars in 2009:


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That night Cruz won the Oscar for Best Supporting Actress for Vicky Cristina Barcelona.

29.

Here’s what Prince looked like at the Oscars in 2005:


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Prince won an Oscar for Best Original Score for Purple Rain back in 1985.

30.

Here’s what Denzel Washington with his wife, Pauletta Pearson, looked like at the Oscars in 1991:


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Washington won the Oscar for Best Supporting Actor for Glory in 1990, and would go on to win the Oscar for Best Actor for Training Day in 2002.

31.

Here’s what Grace Kelly looked like at the Oscars in 1955:


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That night Kelly won the Oscar for Best Actress for The Country Girl.

32.

Here’s what Sidney Poitier looked like at the Oscars in 1967:


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Poitier was the first Black actor to win the Oscar for Best Actor for Lilies of the Field in 1963. He would go on to receive an Honorary Oscar in 2001.

33.

Here’s what Shirley MacLaine looked like at the Oscars in 1984:


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That night MacLaine won the Oscar for Best Actress for Terms of Endearment.

34.

Here’s what Stevie Wonder looked like at the Oscars in 1985:


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That night Wonder won the Oscar for Best Original Song for The Woman in Red.

35.

Here’s what Gwyneth Paltrow and Brad Pitt looked like at the Oscars in 1996:


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Paltrow would go on to win the Oscar for Best Actress for Shakespeare in Love in 1999, and Pitt would go on to win the Oscar for Best Picture for 12 Years a Slave in 2014, and Best Supporting Actor for Once Upon a Time in Hollywood in 2020.

36.

Here’s what Cate Blanchett looked like at the Oscars in 1999:


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Blanchett would go on to win the Oscar for Best Supporting Actress for The Aviator in 2005 and Best Actress for Blue Jasmine in 2014.

37.

Here’s what Regina King looked like at the Oscars in 2021:


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King won the Oscar for Best Supporting Actress for If Beale Street Could Talk in 2019.

38.

Here’s what Daniel Kaluuya looked like at the Oscars in 2018:


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Kaluuya would go on to win the Oscar for Best Supporting Actor for Judas and the Black Messiah in 2021.

39.

Here’s what Julia Roberts looked like at the Oscars in 2001:


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That night, Roberts won the Oscar for Best Actress for Erin Brockovich.

40.

Here’s what Robert Redford looked like at the Oscars in 1981:


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That night Redford won the Oscar for Best Director for Ordinary People, and would go on to receive an Honorary Oscar in 2002.

41.

Here’s what Julie Andrews looked like at the Oscars in 1965:


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That night, Andrews won the Oscar for Best Actress for Mary Poppins.

42.

Here’s what Raquel Welch and football legend Joe Namath looked like at the Oscars in 1972:


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43.

Here’s what Diahann Carroll looked like at the Oscars in 1969:


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44.

Here’s what Sandra Oh looked like at the Oscars in 2020:


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45.

Here’s what Anna Paquin looked like at the Oscars in 1994:


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That night, Paquin won the Oscar for Best Supporting Actress for The Piano at only 11 years old.

46.

Here’s what LaKeith Stanfield looked like at the Oscars in 2021:

47.

Here’s what Zoë Kravitz looked like at the Oscars in 2019:


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48.

Here’s what Natalie Wood and Warren Beatty looked like at the Oscars in 1961:


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Beatty would go on to win the Oscar for Best Director for Reds in 1982 and the Irving G. Thalberg Memorial Award in 2000.

49.

Here’s what Isaac Hayes looked like at the Oscars in 1972:


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That night, Hayes won the Oscar for Best Original Score for Shaft.

50.

And here’s what Audrey Hepburn looked like at the Oscars in 1954:


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That night, Hepburn won the Oscar for Best Actress for Roman Holiday, and she would go on to receive a posthumous Humanitarian Oscar in 1992.

Kenneth Proto

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