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The Most Daring MTV VMA Fashion Of All Time

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September 11, 2021 - Jamie McCarthy/Getty Images North America more pics like this »
2. Billie Eilish 2021
Billie Eilish loves to go for unexpected looks at awards shows. While her peers rocked cleavage and skin-tight mini dresses, the singer went full fall in a black sweater dress with slouchy socks paired with heavy embellished combat boots. She was still sporting her new platinum locks (instead of her former black and green hair) and appeared with very natural makeup. You've got to admire her commitment to comfort on the red carpet.