This article examines struggles for masculinity among Herero elders, South African colonial administrators, and the Otruppa, a Herero youth society that appropriated a German military aesthetic, in Namibia between 1915 and 1949. As previous scholars have argued, masculinities are mutually constituted through competitions for authority, though dominance is rarely achieved. Such contestations were integral to processes of Herero societal reconstruction following German rule and during South African colonial state formation, beginning in 1915. Different generational experiences of colonial violence and the destruction of the material resources that undergirded elders' authority led to conflicts between elders and youths over how to define Herero masculinity and negotiate authority in a rapidly changing colonial milieu.