The dearth of research on style shifting in African American English (AAE) during the early lifespan has left a number of unanswered questions related to the acquisition of and the ability to shift speech styles. This presentation focuses on several of these questions, including when stylistic shifting is initiated, whether there are differential patterns of stylistic usage among children and adolescents, and how stylistic facility relates to school achievement and literacy. It further considers the influence of social, demographic, and self-regard factors to determine how they affect style over time. As a basis for addressing these issues, this research utilizes data from a unique, longitudinal study of AAE and literacy. The analysis compares formal and informal language data from a sample of African American speakers collected at three temporal data points (Grade 1/2 (N=73); Grade 6 (N=125); and Grade 8 (N=164)) to compare linguistic behavior throughout the elementary and middle school years. Language samples representing different situational contexts were analyzed in terms of 42 morphosyntactic and phonological AAE features to determine the overall difference in dialect use across time and situation. Analyses suggest that while there is a range of individual variation in the early use of style shifting, speakers progressively engage in an overall expansion of style shifting over time. Further investigation of the influence of gender, mother's education, social contacts, school demographics, and the child's score on a racial centrality index identifies which factors have a greater impact and how the relative influence of these variables evolves during childhood and adolescence. Tests of the interaction effects of these various social, personal, and demographic factors indicate that while certain factors are significantly related to style shifting, the influence of others is instead associated with speakers' overall dialect use.