This article examines visual representations of kisaeng (courtesans) in photographs and photo postcards, produced by Japanese entrepreneurs and kisaeng themselves, by viewing them as a contentious site of the historical memory of Japanese colonialism. It problematizes the nation-focused narratives on kisaeng in postcolonial South Korea as these narratives fail to recognize the complex dimension of the image-making process that cannot be fully grasped by the dialectic of the colonial aggressor and its victim. Instead, this article shows how kisaeng exercised their agency by actively engaging in producing visual images of themselves as a politically conscious response to the colonial reality. The author pays special attention to visual images appearing in the magazine Changhan, which was established by a group of kisaeng, to underscore women’s political intervention in the visual regime of colonial capitalism. The women’s voices embedded in Changhan are crucial, since they not only problematize their othered social position constructed by colonial capitalism and patriarchy but also lead us to investigate their interventions in the politics of representation that moved strategically across tradition and modernity while shifting their position from object to subject, and vice versa, revealing their tactical maneuver of the technological implications of visual politics.