Looks at the performance of tomboy identity in Joan Anim-Addo's collection of poetry Janie, Cricketing Lady and Margaret Cezair-Thompson's novel The Pirate's Daughter. Argues that the ongoing affects of colonialism and patriarchy in the islands of Grenada and Jamaica, shape the life narratives. To understand the way in which affect can be expressed through tomboyism in Caribbean societies, it is necessary to look at color and class alongside gender in the context of Caribbean creolization.