May 18, 2008 - Charley Gallay/Getty Images North America more pics like this »
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.