Kahlo painted Self-Portrait with Cropped Hair shortly after she divorced her unfaithful husband, the artist Diego Rivera. As a painter of many self- portraits, she had often shown herself wearing a Mexican woman's traditional dresses and flowing hair; now, in renunciation of Rivera, she painted herself short haired and in a man's shirt, shoes, and oversized suit (presumably her former husband's).
Frida Kahlo said regarding her painting ""I never paint dreams or nightmares. I paint my own reality. The only thing I know is that I paint because I need to, and I paint whatever passes through my head without any other consideration."