Events in the early twentieth century had profound impacts on American culture. The most indicative shift of the time is that of the flapper, a young woman drastically different from her more conservative predecessors at the turn of the century. While the Gibson girl, images of the Modern American woman created by Charles Dana Gibson, is primarily described as the predecessor to what would become flapper culture, it is immediately apparent that there must have been intermediaries as the transition from Gibson to flapper is not one-to-one. This ideal image of the Gibson girl, while remaining feminine, laid the groundwork for more independent and confident women that would be seen during the height of flapper culture. This article will examine one such pioneer Alice Roosevelt, daughter of former president Theodore Roosevelt. By doing so, this oral presentation will examine Alice Roosevelt’s ties to the Gibson girl while examining her actions and behaviors that would go on to resonate with flapper culture, through interviews with Alice and contemporary sources to flapper culture, such as the works of F. Scott and Zelda Fitzgerald.