This essay looks to cruising (i.e., searching for and engaging in sex in public and quasi-public spaces) in order to reexamine our understanding of sartorial extravagance, masculinity, urbanism, and sexuality in the early modern period. Attending to aspects of Ben Jonson’s Every Man Out of His Humour (1599) that seem at odds with the play’s satiric aims, this essay queries critical assumptions that the play and early modern culture speak univocally and unequivocally in condemnation of extravagant male dress. In Jonson’s representations of extravagantly dressed men finding pleasures in urban spaces otherwise hostile to their practices, there are traces of utopian fantasies about and longings for queer public sexual culture. The historicism this essay proposes is “cruisy” not only because it offers a reading of representations of cruising, but also because it derives its methodology from those representations. The essay demonstrates that by thinking through the relationship of cruising to historicity, spatiality, and textuality, queer readers of early modern culture can forge forms of historicist engagement with literary texts that also speak to twentieth and twenty-first century issues involving the politics of sexuality.