This article examines male cross-dressing in Italian Renaissance comedies with a particular emphasis on Il Ragazzo by the Venetian writer Lodovico Dolce. Without challenging the traditional readings of cross-dressing plots that view their licentiousness and their reversals of gender and sexual roles as comic conventions typical of this genre and of the festive time of carnival, it is suggested that such plots offered a particularly rich opportunity for imaginative play. This study posits a connection between a historical social formation—the changing sexual status of young males as they pass from feminized youth to full masculine adulthood—and the representation of male characters dressed as women. The texts of these comedies, seen in their social and historical context, provide an interesting basis for discussion of issues of gender and masculine identity in a highly structured patriarchal society.