The law is full of labels which serve to define the concept, person or principle under consideration. These labels have their uses but can also create straight-jackets when applied in different social and cultural environments. This paper considers some of the challenges posed by groups of people in the Pacific countries of Samoa and Tonga. A variety of labels may be used to describe such people: transgender; gender-liminal; transvestite; gay, but none fully encompass what it is to be fa’afafine or fakaleiti. These individuals are both integrated and marginalised in their island countries and among the Polynesian Diaspora. They have a place in customary society, but are also influenced by the more global contemporary picture. They are therefore part of tradition but also symbols of change. The legal environment in which they lived is shaped by colonialism but there are also neo-colonial forces at work which threaten and shape their identity. In many respects therefore, they find themselves between two worlds: gender enlightened and gender repressed.