Postsecondary delay in the U.S. is a topic that has generated interest in the field of higher education in recent decades. Seventeen percent of U.S. students under the age of 24 who began their postsecondary education in 2004 delayed their entrance for some period of time. At the national level, studies have indicated that students who delay are not only at a disadvantage in terms of their pre-college experiences, including lower socioeconomic status and lower levels of academic preparation and achievement, but also are less likely to enroll in a baccalaureate granting institution and complete a bachelor's degree. Another vein of higher education research, supplemented by promotion from popular media, has reported a host of positive effects associated with delaying specifically for a "gap year," or an intentional, one-year delay for the purpose of personal growth and learning, including travel, work and/or service work. Although gap year students have been reported to come from privileged backgrounds, this type of delay has been associated with higher academic performance and increased maturity in college. Consequently, there remains a significant disconnect in the literature that would explain how the reported positive effects of delaying college specifically for a gap year co-occur with negative effects found to be associated with delaying postsecondary education in general, observed on a national level. This dissertation is comprised of three papers that focus on different aspects of postsecondary delay in the U.S. The first paper utilizes a large-scale national data set to describe the delay practices of students in the U.S., paying particular attention to the reasons students choose to delay and how different types of students delay for different reasons. This paper also identifies students' pre-college characteristics that predict delay choice. Findings show that there is considerable variation in student characteristics associated with different delay reasons. The second paper uses propensity score matching to create matched samples of students who delay for different reasons and immediate enrollers, to examine how the effects of delaying vary by students' reasons for delaying. The results indicate that when all other factors are equal, delaying for travel as compared to delaying but not for travel has a positive effect on students' academic outcomes and measures of civic engagement six years after starting postsecondary education. Specifically addressing the finding that travel has a positive effect during a delay, the third paper offers findings from interviews of students participating in gap year programs in Ecuador in order to examine the nature of their experiences. This study contributes to existing literature and the field of higher education by disaggregating postsecondary delay in the U.S. and examining the students and outcomes associated with delaying for different reasons. In addition, this study expands existing frameworks for understanding both the delay and gap year choice processes and how delay and specifically gap year experiences may serve in supporting, student success, overall well-being and development.