Although a mainstay of popular fashion discourse, the notion of “figure flattery” is an enduringly neglected concept within the field of fashion studies. The fact that it is such an overlooked concept, however, perhaps testifies to the fact that it is such a nebulous construct. For instance, the overt concern with “figure flattery” so pervasive within contemporary fashion discourse has its precedent in the early-twentieth century preoccupation with looking “smart.” This article thus seeks to at least partially fill this gap through a close examination of the discourse of the stoutwear industry—the precursor to today’s “plus-size” fashions—between the years 1915 and 1931, or the peak of this niche industry’s production. Situating the stoutwear industry within the socio-historical context of America’s emerging consumer culture, as well as the growing stigma of overweight in the 1920s, this article will principally focus on how, by invoking the principles of Gestalt Psychology and various modernist design concepts, everyday stoutwear advertisements promised miraculous slenderizing effects without the need for invasive weight loss. Through a close reading of extant advertisements and industry trade journals, this article therefore will show how stoutwear was made not merely to fit the stout body—a body that was relegated to the margins of the American ready-to-wear industry with the advent of standard sizing in the early-twentieth century—but to also help the wearer to “fit in.”