Brewster worked for the Federal Bureau of Investigation as a file clerk in the early 1960s, until he was fired for being a homosexual. In the 1970s and 1980s, he published Drag magazine.
Brewster owned Lee's Mardi Gras Boutique, a clothing store in a loft on West 14th Street in New York City's Greenwich Village. The store catered heavily to drag performers. He announced its opening on October 31, 1969 at a ball he was hosting. He described it as the first one devoted to cross-dressers. Initially the business was mail order based, but after so many people began coming directly to his apartment, he opened a store around the corner from his Hell's Kitchen apartment. It included a bookstore with a comprehensive collection of books on topics related to transvestites. The store moved several times before arriving at its location on West 14th Street. His boutique made efforts to provide privacy to its customers, including never having a street-level entry. However, some customers have been public about utilizing the store. Among its public and notable customers were Lady Bunny, and costume designers for The Birdcage, To Wong Foo, Thanks for Everything! Julie Newmar, and Tootsie. Brewster described his clientele in an interview in The Village Voice saying, "Half of my clients are respectable-looking businessmen," and that they were "very normal, but they know better than to present that side of themselves."
Drag performances
Brewster staged numerous balls and often performed as a drag queen. Following the tradition of old-time drag performers, Brewster preferred to be called by male pronouns, rather than female pronouns, as has become more popular in modern time.
At his first ball in February 1969, he announced plans to form what would become known as the Queens Liberation Front, with October 31, 1969 to be its formal founding date. Lesbian Feminist Liberation opposed the performance by drag queens at the 1973 LGBT Pride March in New York City. As they passed out flyers, Sylvia Rivera, of Street Transvestite Action Revolutionaries, took the microphone from emcee Vito Russo and spoke against the sentiment and spoke of the harassment and arrests of drag queens on the street, some of whom had been involved with the Stonewall riots. Lesbian Feminist Liberation's Jean O'Leary then insisted on responding by denouncing drag as misogynist and criticizing the march for being too male-dominated. This prompted Brewster to denounce anti-transgender lesbian feminists. The increasingly angry crowd only calmed when Bette Midler, who heard on the radio in her Greenwich Village apartment, arrived, took the microphone, and began singing "Friends". This was one of many events in early 1970s where lesbian and transgender activists clashed.
