Transformation

When it comes to lipstick, Anne Hathaway was a prodigy. "My first play at the stuff was in my mother's bathroom," she has said. "I wanted big lips, so I took her red lipstick and proceeded to run it all over my face. I was five." The 27-year-old one-time Oscar nominee has remained a fan of the classic lippy, drawing comparisons to Hollywood legends. "Her porcelain skin and amazing features give her an Ava Gardner quality," says her stylist Rachel Zoe. With kindergarten—and Mom's hand-me-downs—long behind her, Hathaway is a true 21st-century stylesetter.

1997: The freshman at Millburn High School in New Jersey was a natural beauty.