Scholars generally agree that financial deprivation negatively affects students' educational outcomes. However, while absolute levels of resources are important, individuals' perceived relative economic wellbeing also shape their educational outcomes. This article asks whether attending school with peers from comparably richer families is related to adolescents' educational expectations, aspirations, university plans, and university attainment. We test the relative deprivation theory by comparing three different forms of the Yitzhaki Index. Data for this study comes from the Taiwan Youth Project, which consists of two cohorts of adolescents (N = 5098) from 162 middle school classrooms. The results show that relative deprivation in the classroom is negatively related to students' educational expectations, aspirations, and plans to attend university. Yet, relatively deprivation is not associated with higher educational attainment when controlling for absolute measures of family background. These results highlight the need for a more nuanced understanding of perceived relative economic disadvantages in shaping student outcomes.