News reports and critical reviews of the 2010s have repeatedly reported that men are bound by traditional male roles at work. This study examined the kind of organizational factors that facilitate male roles expectations by men's supervisors and how these expectations impact their emotions and mental health in the workplace. The results show that these expectations existed in workplace environments that foster strong machoism and male dominance and a less inclusive work environment. Results further show that regardless of male roles attitudes, when supervisors required men to be manly, it decreased positive emotions felt about the job, and increased the levels of distrust felt toward their boss and discomfort within their workplace, which exacerbated their mental health. This research promotes the integrated understanding of gender harassment and organizational research and discusses prospects for future studies.