Both theoretical and empirical research has recognized the importance of contextual factors for Mexican-origin youths' educational outcomes. The roles of parents, teachers, and peers have been predictive of Mexican-origin youths' academic achievement, educational expectations, and decision to enroll in postsecondary education. However, few studies have examined the interdependence among sociocultural context characteristics in predicting Mexican-origin youths' educational outcomes. In this dissertation, two studies address this limitation by using a person-centered analytical approach. The first study identified profiles of Mexican-origin youth using culturally relevant family characteristics. The second study identified profiles of Mexican-origin youth using culturally relevant school characteristics. The links between profiles and youths' academic achievement, educational expectations, and postsecondary enrollment were examined in both studies. Overall, this dissertation contributes to the growing body of literature that aims to understand risk and protective processes related to Mexican-origin youths' academic achievement, educational expectations, and postsecondary enrollment.