In the early 1920's androgynous fashion was in vogue among upper and middle class women. Women like Romaine Brooks, and the subject of this portrait, fellow artist Hannah Gluckstein embraced this move toward broader fashion as well as questioning gender roles. Gluckstein described her new style saying —
"I am flourishing in a new garb. Intensely exciting. Everybody likes it ... I hope you will like it because I intend to wear that sort of thing always."