Wiley finds his models in everyday encounters in the streets and invites them to collaborate with him on a formal portrait. The sitters’ individual choices in fashion and style are a key aspect of the painted portrait and contrast with the formal poses of the historic portraits which serve as a starting point for Wiley’s work.
Instead of painting a suit of armor, Wiley’s Saint George wears colorful patchwork “Madras shorts.” The colorful printed cotton fabric originated during British Colonial rule in Madras (now known as Chennai), India, and spread through trade across the British Empire. The fabric came into fashion among American tourists in the Caribbean in the 1930s and was adopted by Ivy League students back in the U.S., making the pattern a preppy American staple of the mid-20th century.