Nick Wooster was born in Salina, Kansas on July 2, 1960. At 16, he began working at a local clothing store Joseph P. Roth and Sons. He entered the University of Kansas in 1978, where he studied journalism and advertising. After graduation in 1982, Wooster moved to New York City, where he took a job at advertising agency Saatchi & Saatchi. Later he became an assistant department manager for the Saks Fifth Avenue store chain, and in 1984-1985 he worked as account executive at New York Magazine.