Using a legal-consciousness approach, this paper discusses the issue of stigma and law from the perspectives of a group of older homeless people in Singapore. Focusing specifically on the Destitute Persons Act 2013 Rev. Ed. (DPA), the paper shows the different ways in which homeless people make sense of, negotiate, resist or succumb to the stigma of a homeless identity ascribed by the DPA. From these experiences, two fundamental problems with the DPA are highlighted. First, the DPA imposes a homeless identity that is entangled in archaic legal definitions that often do not relate to contemporary experiences of homelessness in Singapore. Second, the enforcement of the DPA legitimises a differential treatment of homeless people, without addressing the broader complexities of homelessness.