The phenomenon of crossdressing has become a new challenge for Islamic law in the modern era, especially as technological and social media developments increasingly blur the boundaries between cultural expression, individual freedom, and religious norms. This study examines how classical Islamic law and contemporary discourse view crossdressing in the context of modern social change. This study uses a descriptive, qualitative approach, with a comparative analysis of classical Islamic sources that discuss the prohibition of tasyabbuh (resemblance between genders) and contemporary Islamic legal discourse, which is more contextually oriented in its treatment of gender expression. The results show that classical fiqh expressly prohibits crossdressing behavior as a form of deviation from the nature and gender identity established by the sharia. At the same time, modern discourse emphasizes the need for a more empathetic ethical approach that considers human, psychological, and social aspects. This study underscores the importance of reinterpreting Islamic law to uphold moral and spiritual values while remaining responsive to the dynamics of gender expression in modern society.