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Defence date: 16 May 2017 Examining Board: Professor Hans-Peter Blossfeld, EUI (Supervisor); Professor Fabrizio Bernardi, EUI; Professor Héctor Cebolla Boado, UNED; Professor Hyunjoon Park, University of Pennsylvania As the saying goes: there are some things that money cannot buy. Yet, scholars have tended to analyze the upper class as a homogeneous group, able to overcome any difficulty that life puts in their way to educational success. Nonetheless, the children of the upper class are subject to the disadvantages of a historically discriminated ethnicity, negatively stereotyped gender, and the boundaries of the institutional framework, among other things. By neglecting the heterogeneity of the upper class, the literature on the Inequalities of Educational Opportunities (IEO) has forgotten to test the limits of class privilege in education. The most crucial point for fully comprehending the research that is being pursued here, is that this dissertation does not tackle whether the rich are simply doing better than the poor in school, or whether the gap between social classes is widening or shrinking. Instead, it focuses on the dynamics and limits of privilege. It analyzes how, in some contexts, the advantaged can be disadvantaged too. In other words, it aims to shed light on what happens when privilege meets disadvantage, and how the perks of being upper class vary among different social groups, such as blacks and whites in the US, or boys and girls in Germany. There are three main lessons to be learned from the three empirical chapters of this dissertation. First, privilege is multidimensional (chapter 3). Second, privilege is dynamic (chapter 4). Finally, privilege is contextual (chapter 5). Lastly, one may wonder why the focus should be on upper-class children since they are, generally, the top performers in any country in the world. The reason is simple; because the dynamics of privilege are part of the IEO puzzle. Only by testing the limits of privilege will we be able to unravel the riddle that IEO poses.