This book takes a critical view of masculinities through an investigation of first-in-family males transitioning to higher education. Drawing on six in-depth longitudinal case studies, the focus is on how young men from working-class backgrounds engage with complex social inequalities, as well as the various capitals they draw upon to ensure their success. Through the longitudinal approach, the work problematises the rhetoric of ‘poverty of aspirations’ and foregrounds how class and gender influence the lives and futures of these young men. The book demonstrates how the aspirations of these young men are influenced by a complex interplay between race/ethnicity, religion, masculinity and social class. Finally, the book draws connections between the lived experiences of the participants and the implications for policy and practice in higher education. Drawn from a larger research project, each case study compels the reader to think critically regarding masculinities in relation to social practices, institutional arrangements and cultural ideologies. This is essential reading for those interested in widening participation in higher education, gender theory/masculinities, longitudinal research and social justice.