This dissertation consists of three essays on adolescents' post secondary education choices and labor market returns. The first chapter analyzes returns to selectivity of four-year colleges by different post-bachelor's degree schooling paths. The second chapter documents the role of family income in college application and enrollment processes including college selectivity choices. The third chapter compares the option values of two-year colleges and four-year colleges for different levels of students' cognitive levels. Existing studies on the returns to college selectivity have mixed results, mainly due to the difficulty of controlling for selection into higher quality colleges based on unobserved ability. Moreover, researchers have not considered graduate degree attainment in the analysis of labor market returns to college selectivity. In the first chapter, I estimate the causal effect of college selectivity on wages including graduate degree attainment. I control for both observed and unobserved selection by extending the model of Carneiro, Hansen, and Heckman (2003). There are two channels through which college selectivity affects future labor market outcomes. The first is the wage returns to college selectivity conditional on graduate degree attainment. The second is the effect of college selectivity on the probability of graduate degree attainment and the wage returns to graduate degree attainment. The results show that graduating from a college of one standard deviation higher selectivity leads to a 3.7% higher hourly wage ten years after college graduation regardless of graduate degree attainment. In addition, a one standard deviation increase in college quality increases the expected returns to graduate degree attainment by 0.8% (4.3% increase in the probability of graduate degree attainment multiplied by 18.6% returns to a graduate degree). Recent studies document the increasing importance of family income in college enrollment probabilities over the past two decades in the United States. The second chapter further examines the role of household income in children's postsecondary institution application and enrollment decisions including college quality, using the high school classes of the early 2000s. I find that the family income is monotonically and positively correlated at the extensive margin of higher education (whether or not to apply and enroll in college) even when we control for children's cognitive ability. On the other hand, I find a U-shaped correlation at the intensive margin especially for four-year college students in terms of average applied, or enrolled, college quality after controlling for children's cognitive ability. These findings highlight different roles of the family income in college application and enrollment stages between extensive and intensive margins. In order to boost the number of skilled workers in the United States, policy makers are paying increased attention to the role of community colleges. Traditionally, researchers have studied community colleges in the context of vocational training, or as a budget friendly alternative for the first few years of a four-year college education. The third chapter examines the undocumented value of two-year colleges, namely, the option value incorporating the uncertainty in degree completion. The empirical results show that expected wages of enrolling at four-year colleges are strictly higher for all types of students than those of enrolling at two-year colleges. This is mainly because of the low associate's degree completion probability. These findings suggest that four-year colleges are strictly better than two-year colleges on expectations for all types of students. In order for two-year colleges to serve as a provider of wider options for individuals who have not yet decided whether to pursue a bachelor's degree, it is crucial to improve degree completion rates in these institutions. [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.]