Ellen DeGeneres
The 54-year-old comedian host makes menswear look chic every day on The Ellen DeGeneres Show. DeGeneres styles tailored blazers, sweater vests and classic sneakers to give off her casual, yet professional vibe. “I never thought I was supposed to dress a certain way or be a certain size,” she told Shape magazine in 2010. “I never put that pressure on myself, and no one ever put it on me.”