What to wear: Famously known for her cynical commentary on American life as a New Yorker, Fran Lebowitz is an actor, author, and public speaker. She's been the voice to a lot of political issues and made it onto talk shows such as Jimmy Fallon's and has even scored imitation status on SNL. To channel Fran, wear a black suit with a white button-down shirt, and wear your hair down. Add glasses to complete the look.