The biggest night in Hollywood is fast approaching after a long and juicy award season is trailing behind us. The Oscars fashion is something that demands a few moments of silence, from the chic look pulled by Martha Plimpton, to the outrageous and deranged (in the best possible way) looks served by Cher to the surrealism of Björk's iconic outfits. Today, we're looking back at the best looks of the Oscars from the years gone by before the 95th Academy Awards take place. Find them below.
1. Martha Plimpton, 1989
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Attending as the date of River Pheonix and looking the chicest there ever was, we have Martha Plimpton's look from 1989. She wore a 1930's vintage cream satin gown. Fun fact: she bought this dress on the day of the Oscars. A last minute, chaotic queen after our own heats.
2. Björk, 2001
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Bkörk's 2001 dress was surrealist, humourous and memorable. Hated at the time, but widely remembered now as one of the most iconic outfits in Oscar history. Designed by Marjan Pejoski, it was the last piece in a trilogy, after the pink lantern dress for Cannes, and the sequined skirt Golden Globes look.
3. Lauren Hutton, 1975
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Lauren Hutton came joyful and very tanned in 1975, wearing a sherbert-coloured Halston gown with a fox fur. The fur wouldn't fly in 2023, but it was the 70s after all.
4. Cher, 1986
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Cher wearing Bob Mackie, MVP of the Oscars 1986. She didn't win this year but she won the outfit. One of the only people to get her abs out at the Oscars. Her influence rings on.
5. Diahann Carroll, 1969
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Diahann Carroll wore a fabulous sheer, glittery Kaftan, with a blush-coloured interior dress in 1969. Designer, unknown.
6. Matt Stone and Trey Parker in (?) 2000
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South Park creators Matt Stone and Trey Parker on acid at the 2000s Oscars.
7. Celine Dion, 1999
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Celine Dion, Galliano for Dior in the backwards Tuxedo suit is giving. It's all about the back, receiving public backlash at the time. Compared to what else was on the red carpet at the time, this was quite a scandalised look.
8. Julia Roberts, 2001
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Julia Roberts wore this unforgettable black and white velvet and satin vintage Valentino gown for her first-time Oscars win for Erin Brockovich.
9. Grace Kelly, 1955
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Grace Kelly at the 27th Academy Awards in 1955, when she won the Oscar for best actress for her role in Country Girl. She was wearing a celadon satin gown designed by Edith Head.
10. Billy Porter, 2019
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Billy Porter in Christian Siriano gown/tux in 2019 is one for the history books. Iconic in every way.
11. Cher, 1974
Cher again in another colourful Bob Mackie look, at the 1974 Academy Awards. It was colourful and playful, adorned with sheer flowers.
12. Tilda Swinton, 2009
Always the risk taker, Tilda Swinton showed up at the 2009 Academy Awards in her Lavin two-piece. The silhouette was regal and elegant and mesmerising, with a chicness that could kill.
13. Gwyneth Paltrow, 1999
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1999 was the year Gwyneth won Best Actress for her role in Shakespeare in Love. The red carpet saw her wearing bubblegum pink, Ralph Lauren gown. It's gone down in people's memories as one of the most iconic looks and for good reason.
14. Zendaya 2021
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Zendaya took the spotlight on the red carpet in 2021 with her floor-length yellow-hue vintage YSL gown with a cutout at the centre.
15. Uma Thurman, 1995
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A true princess moment in Barar Tfank for Prada in 1995, the lilac dress looks as if it were dipped in diamonds and the light throw gives us major minimalist cinderella vibes.
16. Billie Eilish, 2020
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The iconic slime-green roots of Billie Eilish can't be erased from our Oscars red carpet memory – and this look in particular was a standout. The then-18-year-old arrived in an white tweed CHANEL ensemble, mirroring Eilish's tried-and-true oversized silhouette. Putting her own spin on the House's iconic tweed suiting, Eilish paired the look with black sneakers, fingerless lace gloves, stacks of gold and silver jewellery and long, black nails.
17. Cindy Crawford, 1991
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Crawford has had many iconic red carpet moments over her storied career, but this red Versace gown from the 1991 Oscars – where she accompanied her then-husband Richard Gere – is a standout. In a recent Instagram post, Crawford even stated "It was actually the first time a Versace gown had ever been worn on the red carpet." How's that for a slice of history?
18. Halle Barry, 2002
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While we adore the lilac Valentino gown Berry wore on the Oscars carpet back in 1996, we can't look past this Elie Saab gown she wore in 2002 when she became the first black woman to win the Oscar for Best Actress for her role in Monster Ball. It's an iconic moment in Oscars history (long, loooong overdue), but damn she looked gorgeous while accepting that award.
19. Winona Ryder, 1994
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Our crowned queen of the 90s, Winona Ryder, wore this stunning white beaded gown. The actress admitted she once wore a $10 dress to the Oscars, so you be the judge on whether this was the one.
20. Nicole Kidman, 1997
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Nicole Kidman wore this yellow floor-length Dior gown to the 1997 Oscars, design by John Galliano, who was at the helm of the French fashion house at the time.
21. Cara Delevingne, 2023
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Cara's return to the red carpet in this dramatic Elie Saab red gown with open leg and tie shoulder was everything we could have asked for and more. Paired with glittering Bulgari jewels? It was a match made in heaven.
22. Timothée Chalamet, 2022
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One of the most interesting men on the red carpet is Timothée Chalamet, who never opts for the boring black suit option (and can we just say, thank you!). In 2022, Chalamet opted for this glittering custom Louis Vuitton pants and cropped jacket – sans shirt. We love the lace sleeve details, and of course, the Panthère de Cartier pendant to round out the look.
Now that you've seen all the looks, you may want to check our pick for the best Oscar moments of all time.
