Prostitution policy in the Netherlands is considered at the vanguard of legalised commercial sex. It has also proven to be innovative when addressing forms of sex work outside the realm of regulation. One type of commercial venue set up by city governments, are streetwalking areas, called zones. These sites are designated to accommodate drug-addicted female street-prostitutes as a method for removing them from red light districts where sex work is heavily regulated and frequented by tourists and clients alike. Over time, the zones have drawn other social groups such as transgendered and undocumented migrant sex workers, who are not drug-addicted but seek the site as an alternative to working in prostitution windows or private clubs. This study focuses on transgendered streetwalkers and explores how they make social meaning of their work, challenging the amount of symbolic capital assigned to this type of sex work, maintaining clientele relations, and performing transgendered identities. In particular, this chapter is a snapshot of a form of street prostitution that represents a crucial step in the social development of state-regulated prostitution in the Netherlands. It also suggests that many transgendered streetwalkers attach a positive value to their use of the site, countering what many window prostitutes, sex-worker advocates, and scholars (Dworkin 1987; MacKinnon 1991; Barry 1995) assign as a negative form of commercial sex (Gregory 2005).