This paper examines the ugly effects of colonial legacies on Caribbean women. It adopts the postcolonial feminist theory and textual analysis method to analyze five selected stories from Stories from Blue Latitudes. These stories are: Alecia McKenzie’s “Firstborn”, Donna Hemans’ “Mother’s Collections”, Michelle Cliff’s “Transactions”, Velma Pollard’s “Smile (God loves you)”, and Sharon Leach’s “Sugar”. This manuscript demonstrates the uniqueness of the experiences of the Caribbean (Third World) woman. It states unapologetically that the harrowing conditions of excruciating poverty, brazen sexual abuse of the girl child, and the matrifocal family unit are deeply rooted in the relations between Europe, America, and the Caribbean Islands. This research submits that it is too pretentious to conclude that the brand of feminism championed by the Western woman is aimed at addressing the global challenges confronting woman. Unlike her European counterpart, the Caribbean woman believes that she has had an uneasy past that continues to trail her social, economic, and political life.