Self-portraits were created throughout the career of British painter George Chinnery. Among all the existing self-portraits of Chinnery, the oil painting Self-Portrait created by Chinnery around 1840 and collected by the National Portrait Gallery in the UK is the most famous one. Based on previous academic research on Chinnery’s self-portraits, this paper first conducts a picture analysis of Self-Portrait, and then focuses on the two landscape paintings that appear in the artwork. Combining Chinnery’s life experience, artistic creation and psychological condition, as well as the social environment he lived in, this paper analyzes how Chinnery’s choice and treatment of the two landscape paintings in the self-portrait helped to shape Chinnery’s personal image, thereby revealing Chinnery’s unremitting pursuit of landscape painting while being a successful portrait painter.