4. Julia Roberts, 2000: The leading lady won Best Actress for her convincing Erin Brockovich portrayal, and made a statement in a black and white vintage Valentino. 6. Halle Berry, 2001: She may have won Best Actress for Monster’s Ball, but Halle Berry didn’t achieve Best Dressed honors in her revealing Elie Saab, which featured floral embroidery.
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