In 1991, Gwyneth made her feature film debut in 'Shout' with John Travolta and also made her first appearance on ET when she graced the red carpet of 'The Prince of Tides' premiere flaunting long locks and short shorts at 19.
Gwyneth lightened up five years later, going blonde at a charity event in New York. By that time the actress had already made a name for herself in Hollywood, having starred in movies like 'Se7en' opposite her future fiance Brad Pitt.
Brad and Gwyneth wore coordinated coifs to the premiere of 'The Devil's Own' in 1997.
After her highly-publicized breakup with Brad, Gwyneth went back to brunette and stuck with a dark-colored mane until 1999 when she showed up at the premiere for 'The Talented Mr. Ripley' as a redhead.
Whether fair, red, long or short Gwyneth will continue to lead the glamorous world of Hollywood with her fashion-forward looks. Click the video for more!