This article contributes to recent debates between supporters of the concept of hegemonic masculinity, as exemplified by R. W. Connell, and a new generation of gender scholars, as to how best explain the dynamic and fluid relationships between men, and men and women, in the early 21st century. Here, the author concurs with many of Connell’s critics and proceeds by arguing that recent feminist extensions of Bourdieu’s original conceptual schema—field, capital, habitus, and practice—may help reveal more nuanced conceptualizations of masculinities, and male gender reflexivity, in contemporary sport and physical culture. This author examines the potential of such an approach via an analysis of masculinities in the snowboarding field. In so doing, this article not only offers fresh insights into the masculine identities and interactions in the snowboarding field but also contributes to recent debates about how best to explain different generations and cultural experiences of masculinities.