Stephanie McMahon is known for wearing many (I’m sure stylish) hats in the world of pro wrestling. The daughter of WWE CEO and chairman Vince McMahon, she is not only the WWE’s vice president for creative issues, she crossed through the ropes in 1999 to become part of the WWE’s many story lines. A story line involving her romance with the wrestler Test led to a story line with the wrestler Triple H, which then led to their marriage in real life. McMahon would resurface later as the on-screen general manager of both the Raw and Smackdown brands. Here she is in an unenhanced (ahem) picture from 1994, her senior year at Greenwich High School in Connecticut.