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9 Celebrities Who Took Beauty Risks on the Oscars Red Carpet

Tomorrow, when the year’s top movie stars take to the red carpet for the 2020 Oscars, certain play-it-safe hair and makeup looks—classic chignons, soft smoky eyes—are bound to make an appearance on Hollywood’s biggest night. But thankfully, there are always a few renegade risk-takers who break away from the pack.

Think Angelina Jolie, who made a high-impact statement in 2012 simply by jutting out one toned leg from her Atelier Versace dress—and became a full-blown meme. Women like Cher and Diane Keaton have always marched to the beat of their own drums, and continued to do so at the Oscars, thanks to a fully exposed midriff and rumpled hair, respectively. For other stars, the awards show is an opportunity to play against type: Rooney Mara subverted the ingenue narrative with a blunt black fringe set high above her brows, a tack that Gwyneth Paltrow took a decade earlier when she appeared with a goth slick of black liner that matched her McQueen gown. And in her own impromptu departure from the bombshell playbook, Margot Robbie ditched the screen siren red lipstick in favor of undone waves and a fresh-faced, no-makeup makeup glow.

Then there’s Zendaya, the 23-year-old singer and hair chameleon, whose dreadlocks not only paired beautifully with her Grecian-inspired dress but also sparked an important conversation around the Oscars two years back. Following Giuliana Rancic’s suggestion that the hairstyle may have smelled like “patchouli oil,” Zendaya’s powerful response called for an end to offensive cultural stereotypes and for a celebration of African-American hair on the red carpet. After all, the best rule-breakers are the ones tearing down barriers along the way

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