Since its emergence in the 1920s, the flapper movement has been perceived as an emblem of social freedom. However, the movement’s notions of freedom were idealistic to the point of being fantastical. Flappers and the era’s youth alike, desperate to escape the older generation’s traditionalism, conformed to these ideals as an act of defiance. However, because of the unrealistic nature of the ideals, the followers of the flapper movement shed key elements of their identities and embraced only the traits that they deemed relevant to the movement. In many ways, the flapper movement inhibited self-expression instead of encouraging it. This paper examines the flapper movement’s impact on two groups of people: the flappers themselves and the youth of the 1920s. While the flappers conformed through consumerism and a blatant disregard for social rules, the youth conformed through sexual experimentation and chaotic college parties. Through an examination of relevant literature and second-hand narrations, this paper debunks the one-dimensional view of the flapper movement sustained by popular media. The findings presented in this paper aim to instigate scholarly discussion on the multifaceted nature of flapper and 1920s youth culture, potentially illuminating other oversimplified cultural movements and fostering a nuanced understanding of social history. By challenging the simplistic portrayal of the flapper movement, this research contributes to a deeper understanding of the interplay between societal norms and individual agency.