In the late 19th century Kate Chopin published The Awakening, a controversial novel that shed light on numerous social issues of the Victorian era and served as criticism of the harsh patriarchal ideology that measured a woman’s worth based on her biological ability to procreate. The author provided two different insights into the Victorian society through the character of Adele Ratignolle, a devoted mother and wife and Edna Pontellier, a radical feminist. The author re-examined the fixed idea of womanhood through the character of Edna Pontellier and shattered the misconception that all women are suitable for marriage and motherhood. Characters such as Edna Pontellier paved the way for the creation of a new character in literature, known as the “New Liberated Woman”. In the 1920s Ernest Hemingway brought a new character to the scene, Lady Brett Ashley, who is in contemporary culture referred to as the epitome of the 20th century woman and is one of Hemingway’s most complex female characters. Her promiscuous nature, extroverted personality and refusal to conform to traditional social norms provoked anger amongst the critics and readers, but she still remained the epitome of the modern woman. Each of the aforementioned characters will be analysed in order to provide a deeper and better understanding of how the idea of womanhood evolved from the 1890s till the 1930s.