(2 of 11) Reese WitherspoonSince first debuting in 1991’s The Man in the Moon, Reese Witherspoon has endeared many with her sweetness and Southern charm. This belle’s keen choice in scripts is mirrored by her sophisticated sense of style. Long favoring ladylike gowns and refined separates, Witherspoon never misses the fashion mark. Ocober 1998 For the premiere of Pleasantville, the actress’s vintage gown seems plucked from the film’s '50s-inspired costume closet. Though instead of a beaded clutch, Witherspoon’s then-husband, Ryan Phillipe, serves as her arm candy for the evening.
