With the help of the drama series Gentelman Jack (2019), this paper aimes to emphasize the importance of clothing as a self-expressing tool for nineteenth-century Halifax diarist, Anne Lister, who embraced her queer identity. Furthermore, it also intends to compare Lister’s rather masculine appearance with that of her life-partner’s, Ann Walker’s feminine style by highlighting the differences between the two with the examination of the garments worn by them as indicators of gender role in the Pre-Victorian society.