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).
Kahlo knew adventurous European and American art, and her own work was embraced by the Surrealists, whose leader, André Breton, described it as "a ribbon around a bomb." But her stylistic inspirations were chiefly Mexican, especially nineteenth-century religious painting, and she would say, "I do not know if my paintings are Surrealist or not, but I do know that they are the most frank expression of myself." The queasily animate locks of fresh-cut hair in this painting must also be linked to her feelings of estrangement from Rivera (whom she remarried the following year), and they also have the dreamlike quality of Surrealism. For, into the work she has written the lyric of a Mexican song: "Look, if I loved you it was because of your hair. Now that you are without hair, I don't love you anymore."