This article employs an intermedial approach to explore the interpretative possibilities that arise from the interactions of different media types in two 1922 magazine versions of F. Scott Fitzgerald’s “Winter Dreams.” Intermediality studies the relationship between media with close consideration of their characteristic possibilities and limitations. The magazine, a media product, combines media types such as narrative texts, illustrations, and advertisements, a combination that creates a reading experience of “Winter Dreams” that differs from experiencing it ina collection or anthology. Arthur William Brown provided the illustrations for both publications in question, the New York-based Metropolitan magazine andthe Canadian magazine MacLean’s. Despite having the same illustrator, the first page of each highlights a different aspect of the story: in MacLean’s, the combination of media types teases the reader with a potential love triangle, while in Metropolitan, it anticipates the doomed relationship between Dexter Green and Judy Jones. This article primarily focuses on how these media types engage with the story’s nostalgic theme and mood, and on a contextual level, with the nostalgia that characterized the youth-idealizing Jazz Age. Youth is one of nostalgia’s primary tropes, with the flapper an emblem of ephemeral beauty. In both versions of “Winter Dreams,” the advertisements’ emphasis on youth and aging echoes Dexter’s distress at discovering Judy’s faded looks, and they reflect the collective worship of youth culture in the 1920s.