This article explores the curious intersections of stoutwear design, Gestalt Psychology, and architectural discourse in early twentieth-century American fashion media. In doing so, it focuses principally on trade media, style guides and advertisements that grappled with the perceived flaws of the stout woman’s physique and how sophisticated design principles, if properly handled, could create the appearance of bodily slenderness. By moving beyond the biological determinism of contemporary obesity discourse, this article argues that ideas about stoutness and, more specifically, what constituted a stout body, were produced through attempts to contain, control, and correct the fat, female body in fashion design discourse. By further embedding this research within a broader consideration of the relationship between bodies, dress, architecture, and modernist design thinking, this article argues that the mediums and discourses of fashion can open up pathways for thinking about the body itself as “designed.”