#4 Anna Wintour
One of the most successful high school dropouts, the English editor-in-chief of Vogue has held onto her position with an iron grib since 1988. Anna developed an interest in fashion when she was a teenager. She quit her studies at the prestigious North London Collegiate School and started working in the fashion industry. The daughter of Charles Wintour, editor of the London Evening Standard never even finished high school, let alone college. In 2009, President Barack Obama invited Wintour to participate in the President’s Committee of Arts and Humanities.