The introduction of skinny jeans for men is one of the most significant events in terms of men’s fashion in the 21st century. Although there were negative social connotations linked to men wearing skinny jeans in the past, this practice has become normalized in recent years. This study investigates the role of fashion in social construction of gender; more specifically, using men’s skinny jeans as a lens for studying the relationship between men’s fashion and masculinity in the 21st century North America. Using theories of social construction and gender identity, I employed mixed methods of conducting a survey and follow-up interview. Men across the university were recruited to share their opinion and experiences related to men’s skinny jeans. The case of skinny jeans suggests that men’s fashion has the potential to allow masculinity to evolve in a more inclusive direction.