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1. Charlize Theron
It's hard to believe Theron was ever anything less than fashionable. The Oscar winner told People that back in high school she was desperate to fit in with the popular crowd.
“I wore really nerdy glasses because I was blind as could be,” she said in the 2011 interview. “I wasn’t in the popular crowd. There was a really popular girl at school and I was obsessed with her. I was in tears one day because I couldn’t sit next to her.”
Her love life didn't fare any better. “The boys didn’t like [me],” Theron admitted. “I didn’t have any boyfriends, but lots of crushes.”