Hard-boiled crime fiction is generally set in urban areas in early twentieth-century USA. Raymond Chandler, as a pioneering author of the genre, incorporates gender roles in his portrayals of the criminal underworld in the post-war era. He portrays men and women engaged in law and order in different ways in relation to current situations of the period. Regarding these understandings of gender and crime with Raymond Chandler’s attitude to these concepts in his early writing career, this chapter aims to explore representations of gender roles in his short story “Trouble is My Business” (1939). Chandler’s representations of space are closely connected to gender because spaces symbolize gender identities in their structures. In addition, this chapter also focuses on spatial representations of such depictions of gender identities and how space is understood in relation to gender stereotypes in the story.