Avril Lavigne

Somehow, Avril Lavigne looks younger now than she does in this picture. You have to concentrate really hard to see past the glasses and the outfit, but when you do, you'll see her face is exactly the same. Not a day of all the years that have passed between then and now seems to show on her face, but back then Lavigne was just a small-town girl with a lampshade haircut, and the dress-sense of a librarian twice her age.

From these humble beginnings, Lavigne broke out and became a pop-punk princess, introducing many of her younger fans to the whole idea of rock music. No matter what she does, she'll always be associated with the badly-spelled hit 'Sk8r Boi,' but her contribution to fashion might have been as important as her contribution to music. For a while during the early '00s, it seemed like every teenage girl wanted to dress like Lavigne.

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