This paper contributes to debates about gender and diversity in teaching. Exploring the underrepresentation of males, socially constructed as a privileged group, is a complex task for researchers working within a social justice framework. Drawing on a national dataset (N = 5,627), we explore entry patterns to primary and post-primary Initial Teacher Education (ITE) programmes, socio-demographic backgrounds and career motivations of male and female ITE applicants and entrants in Ireland. Findings point to possible reasons for the underrepresentation of males in primary teaching, including competitive performance-based selection systems, Irish language competency requirements and a predominantly denominational school system. An intersectional analysis demonstrates the diversity which exists among male ITE applicants. New insights into the complexities of male positionalities in teaching can enhance dialectic debates about reasons for and implications of the underrepresentation of male teachers as well as the transformative potential of diverse and 'caring' masculinities for schools and society.