Background: In terms of high school graduation, college entry, and persistence to earning a college degree, young women now consistently outperform their male peers. Yet most research on gender inequalities in education continues to focus on aspects of education where women trail men, such as women's underrepresentation at top-tier institutions and in science and engineering programs. The paucity of research on the realms where women outpace men, namely college enrollment and completion, constitutes a major gap in the literature. Purpose: This article provides an overview of gender inequality in the transition to college and in college experiences by examining the ways that women are advantaged in higher education and the arenas where they still trail men. It also discusses theoretical perspectives useful in assessing the causes of gender inequality and then suggests how future research could advance our understanding of the complex nature of gender inequality in higher education. Research Design: The identification and critical review of research and theories that have been used or that could prove useful in assessing and explaining the complex patterns of gender inequalities in the transition to college and in higher education more generally. Conclusions/Recommendations: Fruitful pathways for future research to advance understanding of the complex nature of gender inequalities in higher education include examining gender inequalities early in the educational life course, attending to gender differences within vulnerable segments of the population who may be particularly at risk for not attending higher education, and investigating how the structure and practices of schooling relate to gender differences in educational outcomes.