In urban Tonga, certain men identify themselves and are identified by others as taking on some attributes of womanhood on a regular basis. This process, however, yields a heterogeneous category of persons, who are variously positioned in the socio‐economic structure and moral order. At one extreme, some transgendered men are highly productive individuals in the market economy, while, at the other extreme, others are principally preoccupied by their sexual conquests amongst non‐transgendered men, which brands them as unproductive consumers because of the economics of casual sex relations. The stereotypes of mainstream society focus more readily on the second pattern than on the first. Stereotypical representations also align transgendered men with modernity and the West, and this association places the target of these stereotypes in a potentially vulnerable position, both symbolically and otherwise. This analysis explores the ethnographic diversity of transgendered identities within a single society, the complex interweaving of symbolic and material forces in defining these identities, and the power of stereotyping in the lives of those who are the target of the process.