Readers of F. Scott Fitzgerald's fiction in the Saturday Evening Post encountered his stories within a matrix of visual materials familiar both in format and in terms of the artists who produced them. “Bernice Bobs Her Hair,” published in the Post on May 1, 1920, is routinely recognized by scholars for helping to solidify the young Fitzgerald's reputation as a social historian for the Jazz Age and its youth. Yet the extraction of the text alone from its original site of publication has caused scholars to overlook the role of the illustrator in this process. While Fitzgerald was still relatively unknown when the story appeared, May Wilson Preston was an established artist who had been depicting, debating, and reframing young womanhood for over a decade, though she is largely unknown today. Far from being incidental, Preston's popularity and status framed and lent credibility to Fitzgerald's story about the first generation of young women granted the rights for which she and many others fought. This article examines the works of both artists to explore how the textual and the pictorial functioned together for Fitzgerald's audiences, and considers the problematic implications of the work of female illustrators being written out of American literary and cultural history.