The flapper was seen as a popular female type of the 1920s of America. This paper examines this prevalent image of a modern young women who had a short but intense life in American culture, by reading some works of Scott F.Fitzgerald. Best known as an epitome and a chronicler of the 1920s, Fitzgerald arguably invented and popularized the flapper image in America. This paper focuses on three short stories collected in Flappers and Philosophers (1920), "Head and Shoulders", "Bernice Bobs Her Hair," "The Offshore Pirate," and The Great Gatsby (1925), his most celebrated work. As is well shown in naming the age as the "Roaring Twenties" and people as the "Lost Generation," the postwar America underwent disorientation, turbulence, and disorder, totally having lost traditional value system. Reflecting such social changes, the flapper, as a type of the New Woman, liberated herself from the constricting identity defined by domestic ideology, and rebelliously defied traditional conventions of female virtues. Fitzgerald created vibrant female characters who are spoiled, sexually liberal, self-centered, and fun-loving, not confined to the home, but enjoy individual freedom. As such, they seemed to overcome the previous conceptions of women as 'invalids' who had been represented to become ill, degenerate, and women as 'invalids' who had been represented to become ill, degenerate, and ultimately die, Fitzgerald has long been misconstrued as a spokesman for celebrating this new type of women, but his attitude was nuanced and ambivalent. He increasingly used her as a symbol not only of freedom but also of social conflict and unrest. Although Fitzgerald himself created a flapper with complexities, a more standardized flapper image instantly allured and influenced young women of the era on a wide scale, and it was popularized and spread by a stream of popular magazines, advertisements, and movies. As its popularity increased, the flapper quickly turned into a stereotypical type of woman who temporarily enjoys freedom and rebellion but finally decides to settle down to a safe home. In short, the flapper was an outright expression of individual freedom and liberated energy in one respect, and yet in the other, she served as a safe receptacle for containing social anxiety and disorder. In the aftermath of its paradoxical cultural significance. the spirit of subversion is safely contained in repetitive literary representations of modern women who are yet invalids and/or die, sexually oppressed by social restrictions which are still to be overcome long after the 1920s.