The significance and relevance of this article is that it identifies and surveys a group of artists who made portraits of Australian Aboriginal women prior to 1960. While the artists are known to the public individually, their acknowledgement as a group who share the same interest in the portraiture of Aboriginal women has not been investigated before. This article explores the historical imaging of Aboriginal women in Australian art and portraiture from 1788 to 1960, a period defined by two distinct phases in relation to Aboriginal people. The first phase from 1788 to the 1930s is characterised by a simplistic interpretation of Aboriginal art and people, which tended to reflect evolutionist and ethnographic influences. The second phase from the 1930s to 1960, is characterised by increased anthropological emphases. When these phases are considered in light of the depiction of Aboriginal women in Australian portraiture, interesting characteristics are revealed. Historical change indicates that by the 1950s more compassionate imaging of Aboriginal women conveys a sense that artistic renditions were also reflective of changing attitudes, artistic styles, unique creative strengths, and the perceptiveness of the individual artist. The article is written by an Aboriginal author. For historical accuracy, some outmoded or racist terms which may be considered offensive when included in other contexts, are used in this article when relevant. (e.g. “mixed-race”, “full-blood”, “half-caste”, “race”, “native”, “white”).