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What 39 Celebrities Wore When They Won Their First Oscar

Hey Gwyneth, can we borrow your dress?

You might not know this about me, but I don’t get nominated for a lot of Oscars. It’s sad, but it’s true. Maybe it’s because I’m not actually an actress, or maybe it’s because the only reason I’m interested in Awards Shows is to see what everybody wears. Whatever the reason, it’s nearly time for the 2020 Oscars and I’m still waiting for an invitation. So, while we sit and wait for the 92nd Academy Awards next week, let’s reminisce about what our favourite screen stars wore when they won their first little golden man. From Regina King’s 2018 win to Audrey Hepburn’s 1954 debut, here’s what the oscar winners were wearing.

Regina King, 2019

Now that is a thigh-split if ever we saw one.

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Glamour Girl Maxi Dress In White

Viola Davis, 2017

Red dresses on the red carpet will never get old. Especially the ones by Armani Privé.

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We Got This Feeling Dress In Red

Emma Stone, 2017

Emma Stone is radiating old Hollywood is this Givenchy Haute Couture gown. TBH, it seems only fair since she accepting the Oscar for Best Actress for her role in La La Land.

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American Hero Maxi Dress In Rose Gold Sequin

Brie Larson, 2016

Only Gucci could make a giant metallic belt look this chic.

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Electric Aura Dress In Cobalt Blue

Alicia Vikander, 2016

If there was ever a dress to make us cry happy tears, this is it. Arguably this is one of Nicholas Ghesquire’s best looks for Louis Vuitton.

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Let’s Pretend Knot Front Dress In Yellow

Lupita Nyong’o, 2014

Move over Cinderella, there’s a new pale blue princess in town and she’s an Oscar winner no less.

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Girls Life Jumpsuit In Light Blue

Jennifer Lawrence, 2013

Never forget J Law falling up the stairs in this Dior creation.

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Always Will Love You Dress In Blush

Anne Hathaway, 2013

Those awkward darts aside, this pale prink Prada dress is honestly the stuff of dreams.

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Still Love You Dress In Blush

Octavia Spencer, 2012

If you’re going to win an Oscar, this is what you wear to do it. Period.

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Together With You Maxi Dress In Rose Gold Sequin

Natalie Portman, 2011

Rodarte dressed Natalie Portman for her role in Black Swan so it’s only fair she wore one of their creations to accept her Best Actress Oscar for the same film.

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Like A Vision Dress In Aubergine Mesh

Sandra Bullock, 2010

This is the moment we fell in love with sequins on the red carpet.

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Get With The Times Maxi Dress In Silver Sequin

Mo’Nique, 2010

Mo’Nique was a full 10 years ahead of her time with this striking cobalt shade we’re all trying to pull off in 2020.

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Shake The World Dress In Blue Satin

Kate Winslet, 2009

So you’re telling me Kate Winslet didn’t win her first Oscar for playing Rose in Titanic. That’s outrageous. At least when she finally won she was wearing Yves Saint Laurent.

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When I Was Falling In Love Dress In Black Satin

Penelope Cruz, 2009

This vintage Balmain ballgown is exactly what I’d want to wear to win Best Supporting Actress.

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Wrap It Dress In Champagne Satin

Marion Cotillard, 2008

This is the mermaid dress that inspired millions of mermaid dresses to come. This Jean Paul Gaultier creation is aquatic perfection.

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Love Dont Cost A Thing Dress In Rose Gold Sequin

Jennifer Hudson, 2007

Jennifer Hudson took home the Oscar for Best Supporting Actress dressed in Oscar de la Renta. Coincidence? I think not.

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Graceful Dancer Dress In Mocha

Reese Witherspoon, 2006

Reese’s look is vintage Dior and honestly, she makes it look as fresh as a daisy.

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Called Out Dress In Gold Sparkle

Cate Blanchett, 2005

Cate Blanchett is making a serious case for only ever wearing pale yellow.

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Let’s Pretend Knot Front Dress In Yellow

Renee Zellweger, 2004

We can’t wait to see what Renee Zellweger wears if she wins an Oscar this year. It won’t be easy to top this Carolina Herrera look.

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One For The Money Dress In White

Charlize Theron, 2004

Charlize would like one serving of ‘I’m a fucking movie star’, ASAP.

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Magic Hour Maxi Dress In Silver Sequin

Nicole Kidman, 2003

Nicole Kidman in Jean Paul Gaultier is exactly why she’s an Australian staple on the red carpet. Love it, love her.

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Never Lose Sight Dress In Black

Catherine Zeta-Jones, 2003

Imagine having your maternity wear made by Versace! Catherina Zeta-Jones makes being nine months pregnant look like a walk in the park (apparently it’s not, FYI).

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At The Altar Dress In Black

Jennifer Connelly, 2002

Ah, the skinny scarf, the most haunted relic of early Noughties fashion. What a mood.

The 74th Annual Academy Awards - Press Room

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Keep In Touch Scarf In Mocha

Halle Berry. 2002

Now, this is how you wear florals on the red carpet.

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Promenade Maxi Dress In Wine

Julia Roberts, 2001

Julia Roberts still has this Valentino dress. She told People she’s keeping it in a box under her bed for her daughter, Hazel.

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Tasteful Dress In Black

Hilary Swank, 2000

Forget the dress, cop a look at that diamond necklace!

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Revolve Around Me Dress In Dusty Blue

Angelina Jolie, 2000

Remember when Angelina Jolie went through a goth phase like the rest of us?

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Enjoy The Moment Dress In Black

Gwyneth Paltrow, 1999

File this under dresses I would happily wear to work every day.

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Can’t Help It Maxi Dress In Blush

Helen Hunt, 1998

Helen Hunt looks so happy with her matchy-matchy shoes and dress by Tom Ford for Gucci.

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Lucky Day Maxi Dress In Blue

Susan Sarandon, 1996

The bronze dress, the bronze shoes, the bronze shawl, the bronze sunnies. I guess bronze was having just as a big of a moment as Susan Sarandon in 1996.

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MinkPink – Getaway Sunglasses In Tort

Emma Thompson, 1993

Why did we stop wearing head-to-toe turquoise? Can we bring it back?

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Solid Plan Maxi Dress In Emerald Green Sequin

Jodie Foster, 1989

Nothing says 1989 like this off the rack number paired with not-so-nude stockings. In fact, I’m pretty sure my mum had the exact same outfit.

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Dani Dress In Blue Lurex

Meryl Streep, 1980

I don’t know what’s more amazing, Meryl Streep’s popped collar or the fact that since 1980 she been nominated for an Oscar almost every single year.

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Corporate Vision Blazer In Cream

Maggie Smith, 1979

Professor McGonagall is almost unrecognisable in this gold dress she wore to take home Best Supporting Actress.

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Diane Keaton, 1978

I firmly believe Diane Keaton still wears this exact outfit out and about. I guess there’s something to say for uniform dressing.

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Class Act Trench Coat In Beige

Julie Andrews, 1965

Mary Poppins came to slay in a simply gorge canary yellow dress.

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Let’s Pretend Knot Front Dress In Yellow

Elizabeth Taylor, 1961

Would you expect anything else but extra and extravagant from Elizabeth Taylor the night she took home Best Actress?

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Grace Kelly, 1955

In 1955 Grace Kelly wore a stunning pastel gown by Edith Head to take home Best Actress for The Country Girl.

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Audrey Hepburn, 1954

Audrey won her first Oscar in 1954 for her role in Roman Holiday (a fab flick, BTW). Her Givenchy look was as chic as ever with a cinched waist silhouette and a delicate boat neck neckline.

Audrey Hepburn Holding Oscar

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Everlasting Gown In White
Words by Emma Roffey and Nathalie King

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