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1999

It was her winning year in 1999, as 26-year-old Gwyneth picked up one of those coveted gold statues for her role in Shakespeare in Love. Her pink-toned makeup perfectly coordinated with her now-famous Ralph Lauren pink gown. Topped off with a classic bun, her look was timeless, but modern.

Source: WireImage
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cloroxcowgirl cloroxcowgirl 5 years
I don't think slicked back hair works for Gwyneth.

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