(May 18, 2008 - Source: Charley Gallay/Getty Images North America) more pics like this »
6. Grecian Gown

Taylor had a tendency to wear gowns that looked a little prom-y, but this Grecian-inspired gown and messy updo looked both young and chic on her. Incidentally, T. Swift won the best new female vocalist award at this May 2008 award show ceremony.
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