This article discusses how residents of early twentieth-century Rio de Janeiro, Brazil, defined vagrancy. Commentators on the 1890 Penal Code sought to explain the terms of the article related to vagrancy, article number 399, and its application. Evaristo de Moraes, a lawyer, essayist, and public intellectual at that time, similarly dedicated several works to this topic, as did journalists and literary writers who worked in the press. But these debates in the lettered realm were not isolated from the views and actions of average citizens, a phenomenon that one can observe by reading the criminal proceedings against women who were arrested for repeat offenses against anti-vagrancy laws. In the interventions and arguments of the accused and their defenders, it is possible to observe how vagrancy took on new meanings and how, over the course of time, the relationship between these women and the world of work evolved.