This dissertation analyzes historical and cultural factors that influenced F. Scott Fitzgerald\u27s portrayal of women in three of his early works. In Sentiment—and the Use of Rouge, This Side of Paradise, and Head and Shoulders, women act as usurpers and destroyers, infiltrating male territory and taking on traditionally male roles. Fitzgerald reacts to changes in the status of women that had been occurring since the late 1800s. But the late 1910s, when the author composed these works, witnessed a hastening of women\u27s progress and an intensification of the male anxiety resulting from these changes. Repercussions of the war in Europe did much to exacerbate men\u27s fears. Here, I examine the many ways in which the war influenced American culture and how Fitzgerald, something of a self-appointed voice of his generation reflected the male panic resulting from changes in gender relations. To do so, I attempt to recover and reconstruct the zeitgeist of the late 1910s through an extensive reading of period print media. Chapter 1 treats Sentiment, one of the few Fitzgerald works to deal directly with the war. American periodicals published many articles dealing with European—and especially British—reactions to the war. Sentiment dramatizes controversies surrounding changes in fashion, war babies, khaki fever, and eugenics. In chapter 2, I discuss Fitzgerald\u27s portrayal of the automobile in Paradise. Fitzgerald documents the new freedoms that young men and women of the 1910s enjoyed and the role the devil wagon —as period sources called the automobile—played in this liberation. The print media of the 1910s celebrated the motor vehicle\u27s role on the battlefield and the woman driver\u27s contributions to the war effort, thus creating an association between women, cars, and battlefield death. In the novel, the car becomes a vehicle of moral and physical destruction. Finally, I read Head as a commentary on gender role reversals during the war, when women invaded traditionally male territory in the workplace. This usurpation of male roles went all the way to the White House: Edith Wilson secretly made important political decisions as her husband Woodrow lay incapacitated after a stroke