Transformation

When it comes to lipstick, Anne Hathaway is 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 25-year-old Get Smart star 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.

1999: The New Jersey native kicked off her career with the TV series Get Real. "I went through all kinds of frosts and glosses during my teens," Hathaway has said of her youthful makeup look.