This paper aims to investigate the terms and conditions of a lesbian gaze and a lesbian spectatorship from a feminist and queer theoretical point of view. The empirical material consists of three paintings by the American artist Romaine Brooks (1874-1970).  Brooks was based in Paris in the early 20th century where she was surrounded by a group of intellectual and usually cross-dressing lesbians. The women within this context are the ones depicted in Brooks? paintings and this makes her one of the first artists in modernity to openly portray lesbian and cross-dressing women.