In this paper, I investigate the characteristics and poverty status of female- and male-headed households in South Africa using nationally representative household survey data from the October Household Surveys (1997 and 1999) and the General Household Surveys (2004 and 2006). This decade (1997–2006) represents a period for which there is an extensive poverty literature documenting (particularly in the 2000 s) an overall decrease in the poverty headcount rate. At the same time, however, there is evidence to suggest that female-headed households have a far higher risk of poverty and that the poverty differential between female- and male-headed households widened over the period. The aim of this paper is to identify some of the main reasons that female-headed households are more vulnerable to poverty in post-apartheid South Africa and why poverty has decreased by more in male-headed households (relative to female-headed households). The study examines the key features which distinguish female- and male-headed households and whether these have changed over time. In order to link these characteristics with the poverty differential between female- and male-headed households, I then examine whether (and by how much) controlling for the observable differences between female- and male-headed households reduces the significantly greater risk of poverty in female-headed households.