Transformation

With her expressive blue eyes and old-fashioned features, Maggie Gyllenhaal has both come-hither beauty and quirky charm. The star sibling (of brother Jake) experiments with both short crops and long locks, but maintains her brunette hue. After all, Gyllenhaal knows the value of natural beauty. As she told In Style, "What's unconsciously beautiful or sexy about you is often the most compelling."

1991: The Harvard-Westlake student wasn't afraid to take a beauty risk. "I wore loads of ribbons in my hair and let them fall in my eyes," she has said.