Gender roles invariably shape the styles of leadership people assume in outdoor education. This research investigates how society's value of masculine leadership styles influence instructor and participant understandings of, and experiences in, the outdoors. Six practiced outdoor leaders were interviewed to critique their gendered experiences within the industry. While each of their stories were singular, collectively, the interwoven threads reveal marked intersectional similarities. The emergent themes observed included: breaking gender roles is a positive; leaders encourage gender incongruency; and, organisations focus on gender-balanced hiring. Interestingly, the findings, which were not overtly apparent to all participants included: female leaders feel the need to prove themselves; and, the mechanisms to better address gender fluidity in the industry are needed. The investigation also revealed unconscious bias and sexist views still prevalent in the industry. These included: the belief that women are less physically able; sexual harassment is normalized; and, working with female instructors can be more challenging. Our study raises questions about the buried dynamics of gender expectations and the undercurrents shaping both participants' and leaders' experiences in the outdoors. Conclusions are drawn which call for reimagining ways of moving our gendered leadership understandings and practices forward both at the coalface and during professional training.