This publication examines, in detail, two extraordinary interrelated works: Picasso’s Woman with a Book (1932) and Ingres’s Madame Moitessier (1844–56). Each painting is explored in depth, illuminating the parallels and differences between the artists’ techniques and creative ambitions. The first essay tells the story of the twelve-year gestation of Ingres’s Madame Moitessier, focusing on the role of drawings in the elaboration of the composition, and of the sitter herself in determining how she was to be presented. The second essay traces the development of Picasso’s Woman with a Book, among the most celebrated likenesses of the artist’s young lover, Marie-Thérèse Walter. In contrast to Ingres’s work, it was painted in just a day or two. The final essay explores, through these two works, the artists’ shared interest in the relationship between nude and clothed bodies, revealing the depth of Picasso’s engagement with Madame Moitessier, which motivates and animates Woman with a Book.