This chapter scrutinizes the relationship between the empirical and perceived linkage of racialized poverty and female sexuality on the one hand and the regulation (legal, medical, and elite-cultural) of women’s bodies in Puerto Rico during the advent of rapid modernization and socio-economic transformations throughout the first decades of the twentieth century on the other. The chapter explore the meanings and apprehensions about modernity and the way they informed the U.S. colonial authorities and ‘native’ social reformers themselves. In the process, it examines the figures that personified these anxieties most clearly: the so-called women of the street. By analyzing the overlap between the ‘public-woman’/‘woman-in-public’ (actual or virtual) and the laboring-poor woman of allegedly loose morals we demonstrate some of the ways in which this moral panic directly interrelated with the claims of the various social sectors within the debate over civil and political rights—notably, woman’s suffrage. It offers an analysis on how this politicized anxiety, in turn, was sexualized and racially imprinted relative to social class.