This dissertation explores the coming-of-age processes of characters that are perceived as marginal as a result of migratory experiences involving the Caribbean and the United States. Through the theoretical frameworks of Cultural Studies, Postcolonial Studies, Gender Studies, Sexuality Studies, Race and Ethnicity Studies, New Historicism, and Narratology, this project addresses issues of race, ethnicity, gender, and sexuality in the works of Edwidge Danticat and Junot Díaz. The characters in Edwidge Danticat’s Breath, Eyes, Memory, The Farming of Bones, and Krik? Krak!, in addition to those in Junot Díaz’s Drown, The Brief Wondrous Life of Oscar Wao, and This Is How You Lose Her experience cultural challenges as a result of their migratory experiences. In the midst of migration involving Haiti, the Dominican Republic, and the United States, these characters discover hegemonic, cultural circumstances with which they find it difficult or impossible to identify. This ultimately creates a crisis of identity as well as considerable challenges that inhibit the coming-of-age process. The migratory characters in these texts ultimately come of age through the moment of discernment in which they discover that complete assimilation to United States cultural communities is undesirable; as is total dissimilation from Dominican and Haitian cultural communities. Through wearing cultural masks that are imposed upon them by the dominant, hegemonic other and cultural masks that are self-imposed, these characters find a way to be empowered amid the migratory circumstances that marginalize them.