Hale began painting her self-portrait in 1884, working on it at her family's home in Roxbury, Massachusetts and at their summer home in Matunuck, Rhode Island. The painting, "Self-Portrait", depicts Hale gazing confidently at the viewer with her right hand dangling slightly over the chair. Dressed in all black, Hale wears a dress with buttons and a fur collar, covered by a loose jacket. Peeking out of a round black hat are Hale's bangs, which at the time were praised as a youthful hairstyle but could also connote promiscuity. Hale seems to be making a fashion statement with her bangs, choice of costume, and the ostrich-feather fan that she holds. When Hale first showed the painting to her instructors in 1885, artist Bouguereau significantly criticized the size and position of the hand and encouraged Hale to make it "prettier". However, Hale did not make any of the suggested changes to the hand, refusing to conform her work to the idealized, academic notions of beauty. The compositional weight of her hand is also notable because it was extremely rare for artists of any gender to portray themselves looking directly at the viewer without any tools to identify their profession.