Latino men hold a contradictory position within patriarchal privilege that offers them advantages yet undermines their racial and cultural capital. Underpinned by Latino feminist masculinities, this phenomenological study explored how participants redefined characteristics of masculinity. This study provides critical insight into how 26 self-identified cisgender men of Latino or Hispanic descent made meaning of their masculinity performance. We offer three prominent findings that illustrate how Latino men deconstructed traditional masculinity and conceptualized an asset-based consciousness: (a) resisting traditional notions of machismo, (b) navigating racial and gendered expectations in academic settings, and (c) challenging cultural and gendered expectations at home. These findings illuminate the identity development process for Latino men as they negotiate their masculinities within different contexts. We provide recommendations for research and practice that encourage further exploration of the nuanced understanding of masculinity and its relation to structures that perpetuate cisheteronormativity, as well as opportunities to further deconstruct masculinity for Latino men.