This article examines how the British colonial administration and the local Chinese population interacted around the issue of obscene prints in 1900s–1930s Singapore, with a particular focus on the policing of the female nude. The notion of obscenity acquired different meanings as prints crossed geographical, cultural, and linguistic boundaries. What was deemed ‘obscene’ in Republican Shanghai or Edwardian London was not necessarily viewed the same way in colonial Singapore, and vice versa. By tracing the contradictory assumptions about the relationship between nudity and obscenity in a multiracial and multicultural colonial context, this article demonstrates that obscenity regulation in Singapore was intimately tied to what Partha Chatterjee has termed ‘the rule of colonial difference’,1 with race being the most obvious marker of difference. On an institutional level, the rule of colonial difference led to a division of regulatory labour that ultimately rendered Chinese salacious materials invisible to the British colonial government in the early twentieth century. In terms of definitions of nudity and obscenity, perceived racial–cultural differences—central to the rule of colonial difference—were used both to justify and to contest the public display of naked female bodies to non-Western audiences. This situates the Singapore case within the broader scholarship on obscenity regulation and colonialism, and offers fresh insights into the difference in imperial models of obscenity regulation. By exploring how obscenity regulation was premised on the process of racial ‘othering’, this article also highlights race as an underexplored factor in existing scholarship on obscenity regulation.