This paper examines how the process of making higher education choices in the United States—whether to enter higher education, attend a particular college, or follow a particular path through college—produces and legitimates social inequality. The paper’s central thesis is that a societal regime of many choices—while serving individual freedom and producing social well-being—produces societal inequality in a way that obscures that process of social reproduction for virtually all who participate in that choice regime. Students often make choices that do not serve their interests as well as they might wish, particularly if students are faced with many choices and do not have adequate information. The incidence of those suboptimal choices is not random but is socially stratified. It is higher for less advantaged people, and unequal provision of good information plays a crucial role in producing those socially stratified suboptimal choices. Secondly, the provision of many choices legitimates social inequality. Seemingly offered many choices in life, both the fortunate and unfortunate in society come to feel that much of the inequality they experience is due to their own actions and therefore is legitimate. The paper concludes by offering various prescriptions for reducing the socially stratifying impacts and ideological consequences of a high-choice regime. It lays out how we could more equally distribute high-quality information, nudge students toward better choice making, reduce the costs to students of suboptimal choices, and mitigate blaming self and others by demystifying the nature of choice. In making these arguments, this paper draws on the research literature in sociology of education, behavioral economics, cognitive psychology, and social psychology of inequality.