The decisions that students make about their educational attainment have profound impacts on their future economic, demographic, and social outcomes. These decisions, however, do not happen in a vacuum. There is a long tradition of research in sociology, education, and behavioral economics that has studied inequality in educational decision making and the various factors that contribute to creating, or reducing, this inequality. Despite extensive research, inequality in educational attainment persists. This dissertation takes a multimethod approach to identifying sources of inequality and evaluating policies aimed at reducing it. In three distinct empirical chapters, this dissertation extends the literature on educational decision making, expanding our knowledge of how inequality is created and maintained. The first empirical paper, evaluates two "free tuition" policy designs, informing policy conversations about how to reduce economic inequality in selective college attendance. Proposed "free college" policies vary widely in design. The simplest set tuition to zero for everyone. More targeted approaches limit free tuition to those who demonstrate need through an application process. We experimentally test the effects of these two models on the schooling decisions of low-income students. An unconditional free tuition offer from a large public university substantially increases application and enrollment rates. A free tuition offer contingent on proof of need has a much smaller effect on application and none on enrollment. These results are consistent with students placing a high value on financial certainty when making schooling decisions.The second paper focuses on the role of social context in shaping student decision making. There is a long history of sociological research that identifies the essential role of social forces in shaping educational attainment; however, siblings have been understudied as a direct mechanism contributing to educational decision making, overshadowed by the focus on parents and institutions. Using longitudinal qualitative interviews with 36 high-achieving high school seniors from families with low incomes, I explore the unique role that older siblings play in shaping the postsecondary decision making of their younger siblings. I find that the support provided by siblings is distinct from other social resources. The intensity of the relationship, and the internal and external relevance, or the fact the information shared is recent and personalized to the students' circumstances, each make this relationship unique. By studying only parents or considering only the role of parent educational or economic circumstances in contributing to inequality, we ignore an important source of heterogeneity in the lives of students from families with low incomes. The final empirical chapter describes gaps in postsecondary educational attainment between urban, rural, and suburban communities using student-level longitudinal data from the full population of Michigan public high school students. Using several recent high school cohorts, I document rates of college attendance, college selectivity, and bachelor's degree completion overall and within subgroups, providing updated estimates for urbanicity gaps in college attainment. Thirty-six percent of students from suburban high schools enroll in four-year institutions compared with 33 percent and 28 percent of students in rural and city high schools, respectively. Bachelor's degree attainment gaps are similarly large. There is less racial and economic inequality in college outcomes within rural areas than there is in cities; however, it does not come from improved outcomes among racially minoritized students or those from families with low incomes. Students in rural areas from more traditionally advantaged groups have substantially lower rates of college attainment than their suburban and city peers. Therefore, while media narratives about White, rural students falling behind are not inaccurate, they do not tell a complete story. This chapter highlights some key areas for policy intervention to better target the distinct needs of students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]