This study explores, for the first time, an in-depth analysis of the social and cultural history of the shift dress. It provides a multidisciplinary approach which focuses on the significance of the shift dress in the changing context of women’s work, education and their place in contemporary society in the twentieth century. It also locates the dress’s contribution to elements and processes of modern fashion and beyond, into the broader contexts of American popular culture. From its origins, the shift dress evoked modern ideals. Its simple construction means it was an economical, versatile, and expressive garment. The shift dress’s versatility afforded women the opportunity to move effortlessly between sport, work, and leisure. This thesis argues that its simple form is a blank canvas, which allowed women to express themselves individually and freely while propelling fashion forward in terms of innovation. Throughout the twentieth century, it has been reinterpreted, redesigned and reimagined, with the 1920s and the 1960s especially significant periods for this study. Its adaptability across time periods advanced women in the public sphere and in previously male dominated environments and workplaces. The shift dress allowed women to move away from societal expectations to create their own identity. The thesis contends that as a consequence of its attributes, the shift dress was an important vehicle for the evolving expression of women’s strength and empowerment. It was the first dress to provide women freedom of choice, to allow freer movement, physically and socially, and to express self- identity. It is more than a garment clothing a woman’s body, it provided women a new liberation and a way to be modern. The movement that the dress permitted aligned to the changing place of women in American society. This concept of movement is central to the thesis: the shift dress defines movement on multiple levels. It has moved women forward, it has moved fashion forward, and because of this, it is one of the most significant garments in fashion history.