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These Are All The Most Shocking Looks From The Oscars Over The Years, And Now It's Your Turn To Choose The Most Iconic Ones

I'm still thinking about how Uma Thurman CHOSE to be the worst dressed in 2006.

Alana Valko
by Alana Valko

BuzzFeed Staff

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The 2024 Oscars are just around the corner (this Sunday at 7 p.m., EDT to be exact!), which means it's time to look back at all the surprising, over-the-top, and simply iconic looks from over the years.

Here's how it'll go: I'll show you three pictures of celeb looks from a past Oscars year. Then, your job is to pick what you think is the most daring look. Cool? Let's go!

Three women posing individually, each in extravagant gowns, at a formal event with Oscar statues in the background
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Zendaya in a white top and sequined skirt, Jada in a textured long-sleeved gown with full skirt, Billie in an off-the-shoulder ruffled dress with a train
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Laura Dern in a feathered skirt and long-sleeved dress, Amanda Seyfried in a deep v-neck strapless dress with pleated tulle skirt , and Chloe Zhao in a wide sleeve turtleneck and a line skirt
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Kristen Wiig in a structured dress with ruffled detailing along the side, Janelle Monae in a long-sleeved metallic dress with a hood, and sandra oh in a long gown with floral 3D details and feathered sleeves
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constance wu  in a ruffled shapless gown with tall neckline, billy porter in a tuxedo with a voluminous skirt, and kacey musgraves in a frilly tulle dress
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One celebrity a grass-looking gown with sheer neckline, maya rudolph in a draped cape outfit, and adam rippon in a classic tuxedo with a leather harness
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lady gaga in a gown with a cape and bright gloves, neil Patrick harris shirtless in underwear, and j.lo in a long beaded gown
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lupita in a long deep v-neck gown, Pharrell in a tuxedo with shorts, and liza Minnelli in a draped top with matching satin pants
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halle berry in a beaded gown with a tulle train, Helena Bonham Carter in a velvet dress with a UK flag around her shin, and Jennifer Hudson in a satin mermaid gown
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J.lo in a strapless gown with ruffled train on the side, Ben Stiller with Avatar makeup and suit, Zoe Saldana in a strapless dress with ruffled skirt
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tilda swinton in a drapey top and ruffled skirt, Miley Cyrus in a long embellished gown, and whoopi Goldberg in a long-sleeved cheetah print dress
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michelle williams in yellow ruffled dress with a train, charlize theron in dark long satin dress with a large bow, and naomi watts in a one-shoulder beige embellished dress
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uma therman in a layered asymmetrical dress, diane keaton in a suit, gloves, and hat, and renee Zellweger in strapless gown with a large bow and train on the back
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gwenyth paltrow in a tight top and full skirt, halle berry in a sheer floral top and satin skirt, and a celeb in a rainbow tulle dress
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kate hudson in a sheer long gown with an empire style, bjork in fluffy knee-length swan dress, and Angelina jolie in tailored satin suit
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tyra banks wearing a voluminous strapless princess gown, two men dressed in dresses; and Angelina Jolie and her brother in matching dark outfits
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Celine Dion in chic suit with a backwards blazer and hat, Whoopi Goldberg in an ornate historical costume, and Gwyneth Paltrow in elegant thin strapped gown and shawl
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Sharon Stone in a white top and shiny skirt, Cher in a sheer, embellished gown and headpiece, and Madonna in a shiny dark dress with a high collar, accessorized with rings
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one woman in a midi dress made of metallic dollar bills, uma thurman in a form fittin dress and sheer shawl and another celeb in a checkered skirt and shiny jacket
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cher in two-piece floral dress showing her midriff, her in a bold black ensemble with tall headpiece, and cher in a sheer  black gown with gold accents
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Let me know what you think are all the most daring looks in the comments, or if you have any other iconic looks to add!

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