Beginning around 1918 Weber explored themes related to his orthodox Jewish heritage. Why he turned to religious subjects is not known. Perhaps he was responding to the recent deaths of his parents—his father in 1917 and mother in 1918. The following year he began to paint busts of solitary figures set against a neutral background, a format he continued to explore through the remainder of his career, as seen in both Draped Head and Rabbi.
A contemplative painting overlaid with mystical nuances, Draped Head depicts a woman wearing a plain scarf and modest garb, and posed in a gesture of reflection. Because the subject matter and the simple composition recall Weber's eastern European culture, it was perhaps a visual memory of his childhood. The model might have been Francis, his wife of just a few years.
In Draped Head Weber simplified the woman's facial structure, giving her a mask-like appearance. He reverted to the modernist, figural style he had developed in Paris while under the influence of Matisse and Picasso, whose work at that time was influenced by African and Pre-Columbian art. The solidity and monumentality of the figure in Draped Head also reflects his awareness of the strain of classicism in Picasso's work, especially in the early 1920s.
Duncan Phillips probably first became aware of Draped Head from an illustration accompanying Henry McBride's review of Weber's 1925 exhibition at J.B. Neumann's New Art Circle, and purchased it the following year. Writing in A Collection in the Making, Phillips considered Draped Head "a little masterpiece of tragedy. The tormented soul of a Race speaks through this portrait which carries on the Byzantine and El Greco traditions."