Over the last two decades, scholars have investigated the two-way relationship between gender inequality on the one hand, and economic development and growth on the other. Research in this area offers new ways to address the economic stagnation and crisis developing countries have experienced over the last two decades. This paper contributes to that literature, exploring the channels by which gender inequality affects, and in important ways, constrains economic development and growth in the Caribbean region. It further explores the endogeneity of gender inequality to the macroeconomic policy environment. The paper concludes with a discussion of economic policies that can promote a win-win outcome—greater gender equality and economic development and growth.