This article extends Boudon's positional theory to ascertain how students from different social backgrounds estimate their academic performance and how they translate their choices into the final destinations in higher education in the context of contemporary China. I draw upon empirical evidence from a firsthand survey study involving 2,425 undergraduates from different social backgrounds and from different types of universities. The statistical analyses suggest that students from privileged backgrounds and metropolitan areas are more likely to achieve both the institution and field of study of their choice. Geographical origin is the most consistent factor in predicting the overestimation of academic performance and in successful translation of choices into the final desired destinations. Therefore, I argue there is a meritocratic legitimation of geographical inequality between developed regions like Shanghai and underdeveloped areas through higher education selection.