This article examines how the phenomenon of passing, or playing white, is portrayed in selected South African texts. The findings of two studies conducted in the Cape Town area highlight the particular historical circumstances and factors that gave rise to the incidence of passing in certain areas. The article also draws on theorizing about the phenomenon in African-American literature for an analysis of issues of identity, race and gender. It is argued that passing / playing white challenges racially based constructions of identity in apartheid South Africa and that the texts explore these aspects in a multi-faceted way.