Do people have a right to work on the street? If so, what are the constraints and conditions attached to this right? Historically, municipal authorities have tried several ways to regulate or even prohibit commerce on the streets, by implementing administrative regulation and criminal laws, but neither has proven successful thus far. In fact, in some cases, these attempts have backfired. Constitutional challenges to municipal regulations have paved the way for the incorporation of municipal regulations based on a right to work on the streets. This article seeks to understand and explain how the act of placing a wooden or metal stall over a public space contributes to the development of a regulatory regime that administrates the right to work in an urban space. It further shows how these solutions have been jeopardized by litigation and transformed by recent constitutional doctrines that recognize the right to work on streets. Constitutional courts in Mexico, Colombia, and India have addressed the struggles between the street vendors’ ability to work on public thoroughfare and the municipal regulations that seek to limit street trading. As such, our aim is to analyze the way in which the municipal capacity to legislate, control, and regulate public space has been challenged and constrained by street vendors’ invocation of their right to work in these countries. This will help explain how constitutional courts do actually represent urban governance.