This paper examines the transcultural self-portrayal in the works of Eileen Chang (Zhang Ailing 1920-1995), one of the most important modern Chinese writers of the twentieth century. I argue that Eileen Chang, being a self-translator and bilingual writer, adopts the literary technique of what she calls “equivocal contrast” to construct both an enigmatic and illuminating self-image in her essays, fiction, drawings and her personal eccentric dressing styles. In Looking at Photos (Duijiaoji 1994), which was published the year before her death in Los Angeles after two decades of secluded life, Chang showcases the photographs of herself from childhood into adulthood with captions of autobiographical anecdotes. Furthermore, in her numerous stories and essays, such as “Whisper” (Siyu 1944), Little Reunion (Xiaotuanyuan 2009), The Fall of the Pagoda (2010) and The Book of Change (2010), Chang depicts her transcultural self-image between Chinese and Western cultural negotiations, between her family sagas and her fictional revisitations, and between the public’s gaze and her personal desire of commanding visual attention in various manifestations. The analysis of the imagery of self-portrayal in Chang’s works will give a fascinating picture of this legendary Chinese writer amid cultural hybridization in the twentieth century.