The way that public space is structured has significant implications for identity, social interaction, and participation in society. For those experiencing homelessness, with no or limited private space, survival hinges on the accessibility and livability of public space. However, the increasing privatization of public space in the United States has contributed to the implementation of anti-homeless ordinances in cities, restricting sitting, standing, panhandling, and sleeping in public. This study analyzes data from interviews with housed and unhoused community members, text from a local policy document, and ethnographic observations to explore how boundaries between "insiders" and "outsiders" are drawn in public space and mediated through individual discourse. Our findings suggest that boundaries of exclusion are constructed through dominant narratives that portray the unhoused as a threat to safety and economic vitality, thus justifying the need for regulation and punishment through the criminalization of homelessness. Yet, informants also demonstrate resistance to this narrative by discussing how criminalization of homelessness perpetuates dehumanization, violence, and economic inequality. Policy implications for the regulation of public space are discussed.