This study aimed to test the proposed model of educational aspirations of Taiwanese Aboriginal adolescents by applying the developmental-contextual model of career development as its framework. It simultaneously examined the relationships among the contextual variables (i.e., family socioeconomic status (SES), social welfare resources, parental educational support, and school support), the individual-level variable (i.e., school self-concept), and educational aspirations in the proposed model. Data were collected from a questionnaire survey of 851 Taiwanese Aboriginal senior high school students and were analyzed using structural equation modeling. The findings empirically supported the proposed model which explained 36% of the variance in educational aspirations. We found that educational aspirations were influenced by parental educational support and school self-concept, which were, in turn, influenced by school support and parental educational support; school support and parental educational support were influenced by social welfare resources, which were, in turn, influenced by family SES. Overall, the results confirmed that the proposed model based on the developmental-contextual framework was effective in explaining the development of Taiwanese Aboriginal adolescents’ educational aspirations.