In this paper I consider interfaces between visual and textual representations of the female self in art. I am looking in particular at Gwen John's self-portraits and the letters revolving around them. In this context, there are three thematic areas that I explore: a) questions around portraiture in general and the self-portrait in particular, b) connections between visual images and textual narratives in life-writing research and c) genealogical lines in John's self-representation through her paintings and letters. What I suggest is that John's self-portraits become events for playing with different modalities of self-representation and experimenting with other ways of painting the self, while her letters become texts destabilizing and interrogating conventions of reading the visual. What I finally argue is that the visual turn in narrative research needs to consider carefully discourses and debates in the field of art histories, while the latter have to become more informed in the nuances of life narrative research.