Britney Spears – 37

Nobody thinks of Britney Spears with brunette hair. Having seen her for so long with her blonde mane, we’ve all simply forgotten that some time ago, Spears was a bashful brunette (we’ve also long forgotten the bashful part!). Spears was a sensation with her teen spunk and spirit and she was quite the trendsetter. Spears was also known for her lip liner – true ‘90s style. Things have changed of course, and she has got to keep up with the latest – so in comes the earth-tone lipstick and blonde ‘do! Though we must say, she could carry off either one very well.