The traditional values and beliefs entered a stage of transition at the turn of the twentieth-century: new ideas appeared which challenged the accepted notions of womanhood, introducing the figure of the New Woman who rebelled against the confining patriarchal stereotypes. Situating Kate Chopin’s The Awakening (1899) and Theodore Dreiser’s Sister Carrie (1900) in this context, I am going to explore how the two novels depict the transformation of conventional lifestyles and how they illustrate the radical transformation of female identity from the True Woman to the New Woman ideal. Moreover, the comparison of the novels will also reveal the differences in the two writers’ representations of women’s plight, as both of them express women’s confusion and anxiety about their situations. While Chopin’s novel presents a protagonist (Edna Pontellier) who tries to outgrow the restrictive pattern of married life; Dreiser portrays a single girl (Carrie Meeber) misdirecting her life in the urban world in the belief that she is on the path towards selffulfillment. The novels expose highly debated issues regarding women: roles, family, sexuality, work and the chance to achieve self-awareness.