Penn's mother, Robin Wright, surrendered the role of Maid Marian in Robin Hood: Prince of Thieves due to her pregnancy with Dylan. Penn was born to Wright and Sean Penn in Los Angeles on April 13, 1991, and raised in Ross, a town in Marin County, California. Her father, Penn, is a two-time Academy Award for Best Actor-winner, while her mother, Wright, is a Golden Globe Award for Best Actress – Television Series Drama-winner. She has a younger brother named Hopper Jack. She attended Marin Academy, and dropped out of the University of Southern California after one semester. She spent time living in New York City. Her parents' divorce was finalized in 2010. Before modeling, Penn had worked delivering pizzas, as a waitress, and as a freelance screenplay Editor. She also worked in New York City as a restaurant hostess and an intern at an advertising agency.