Gendered patterns of achievement emerged as a critical policy concern for the small island developing states of the Anglophone Caribbean as early as 1986. Although these patterns are mostly variegated, some males do appear to be disadvantaged on key schooling outcomes as evident in the literacy attainment gap for Trinidad and Tobago in PISA 2009 and PIRLS 2011. Theory explaining patterns in the region has been influenced by simplistic borrowing of ideas and the globalised politics of gender. In this paper, I first analyse the work of major thinkers in the Anglophone Caribbean, exploring insights, contradictions, and silences and then consider the utility of such theory for local policy formulation. This diverse body of local knowledge on the issue provides important and unique insights into a complex policy issue. However, explaining variegated patterns requires new theory that is more nuanced and contextualised, drawn from epistemologically diverse research.