For young men, the transition to adulthood may be a time of heightened adherence to traditional gender roles and norms of masculinity. However, recent research with young men in gender-specific contexts has indicated that some contexts support a construction of masculinity that is more inclusive. Through a theoretical thematic analysis of interviews with young men in their first week at an all-male trade school, we explored if and how participants talked about gender and its role in their lives, how these discussions of gender may reflect individual gender ideologies, and how these discussions may inform participants’ experiences in particular developmental contexts. The themes we identified included the following: Becoming a man as an active process, experiences of male embodiment of size and strength, intersections of school identity and being a man, students’ perceptions of their all-male school environment and what it means to not have female classmates, and their reflections on the parts of themselves they see as feminine. We discuss the implications of our findings for future research with adolescents and young adults in relation to gender, relationships, and professional development.