While young women of 1920’s America were often labeled as flappers based on their glamorous lifestyle and their extravagant looks, studying the representation of New Women in F. Scott Fitzgerald’s The Great Gatsby and Ernest Hemingway’s The Sun Also Rises, I wish to argue that being a flapper is a more complex phenomenon that women could identify with based on their social status, appearance, and life choices. Thus, by examining five female characters from the books in question (Daisy, Jordan, Myrtle, and Catherine from The Great Gatsby, and Brett from The Sun Also Rises), I will classify them into different flapper categories based on the factors targeted above. First, I will go through each category and explain why each flapper character belongs to a specific category. Then, I will explore how flappers were portrayed in both fiction and non-fiction texts throughout the period. Following that, I will look at how the narrators of the stories in question relate to their characters. Along with the analysis of narrator-flapper relationships, I will discern what message the books in fact attempt to convey, taking into account the reliability of the narrators and their representation by the authors.