Objective: The purpose of this study was to investigate how Latino men's conceptions of masculinities influenced their attitudes and behaviors during the transition from community colleges to 4-year institutions. Method: A phenomenological approach was used to explore the lived experiences of 34 Latino men across Texas, California, and Florida. Each participant was interviewed twice; all data were recorded, transcribed, and coded for themes. Results: Findings suggest that, although prior conceptions of masculinities can sometimes provide positive tools during transfer, these conceptions also cause challenges as men negotiate incongruences between their masculine identity and what is required to succeed in college. Participation in on-campus men's groups and student organizations can help Latino students navigate these incongruences and negotiate their own intersectional identities and conceptualizations of masculinities in light of their new environment. Contributions: This study demonstrates that Latino men continue to face challenges related to masculinities and identity conflicts during the community college to 4-year institution transfer process. Future research might further investigate how the multiple, intersecting identities of Latino men (e.g., sexuality, class) influence masculinities and transfer experiences. Implications for practice include a recommendation that institutions consider creating on-campus spaces and learning environments to support men in navigating masculinities.