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The actress turned heads when she turned herself into a brunette for the 1999 drama “Bounce” (which co-starred her on-again/off-again beau Ben Affleck). She also created some buzz when she showed up at the 2000 Golden Globes wearing pants. But if anyone could make the casual look seem edgy and elegant all it once, it's Gwyneth! (1/23/2000)

The actress turned heads when she turned herself into a brunette for the 1999 drama “Bounce” (which co-starred her on-again/off-again beau Ben Affleck). She also created some buzz when she showed up at the 2000 Golden Globes wearing pants. But if anyone could make the casual look seem edgy and elegant all it once, it's Gwyneth! (1/23/2000)

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