A transgender identity is generally understood as a collection of identities (an umbrella term) that incorporates a diverse array of configurations and experiences of gender by those who do not identify with the (imagined) normative cultural constructions of sex/gender associations, or who have a sex/gender identity at odds with the constructed binary-labeled associations of “man” and “woman” as credited (usually at birth) by formal authorities and institutions. As we will show with respect to several regions in the Pacific Basin, a transgender identity can be conceptualized as a movement across (trans) socially imposed cultural boundaries—where gender identities either cross over through boundaries within normative gender constructions (and are thus gender identities signified within normative boundaries)—or where individuals cannot be fully defined by existing constructions of gender (and are thus understood as signified conceptually beyond the boundary). Consequently, there is not one way to be “transgender” as it is not an essentialized experience. Instead, it should be understood as situated across contexts and as related to power relations. This chapter will explore transgender notions of experience and identity in the context of the Pacific Basin, specifically in Tahiti, Hawai’i, Samoa, Thailand, and Southern California. As such, we hope to complicate theories of power and identity, as they are sometimes understood as manifestations of Western theory in the region.