This thorough analysis looks into how mental health is complexly portrayed in Virginia Woolf’s “Mrs. Dalloway” and Sylvia Plath’s “The Bell Jar.” The study examines the topic, character development and individuality, and the touch of autobiographical element used by both authors to illustrate the complexity of mental health through a comparative examination. The goal of the research is to identify the distinctive viewpoints that each author contributes to the understanding of psychological challenges by looking at the cultural and historical contexts surrounding the works. The analysis goes on to explore how gender roles, society conventions, and personal identity affect the characters’ mental health, offering a comprehensive look at the writers’ varied perspectives on what is literature, how to portray and discuss mental health in literature. This research depicts the mental struggle of belongingness to themselves and with the society a well. The present research paper will showcase the importance of identity with concern to mental health and it's issues, it will also look up to the reason through which mental health can be affected like societal pressure and cultural flow of identity. With the help of this Comparative study we I want to portray how both these novel’s characters are created with an autobiographical touch and in what case they differ from each other and at the same time what are the similarities that they are sharing. This paper will also dwel into symbolism and imagery of mental struggle which helps for the better understanding of the characters. The results enhance the understanding of the complex nature of mental health as portrayed in these seminal works of fiction.