Our culture has always embraced fairy tales, which have a strong appeal to people all over the world. Fairy tales such as these are often seen as perpetrators of traditional gender norms. This abstract investigates the complexities between gender identity and fairy tales in the beloved classic fable Thumbelina by Hans Christian Andersen. To illustrate how fairy tales can reinforce or subvert stereotypes about men or women in society, this essay examines some problematic aspects drawing parallels with those in one famous folk tale from rural Bengal, called DedhAnguley from Dakshinaranjan Mitra Majumdar’s collection of children’s stories, ThakumaarJhuli. It also uncovers the gendered issues in Thumbelina’s journey, a journey informed by the protagonist’s relationship with other beings, and her understanding of the make-believe world. It also brings to light the way children’s stories represent gender and how these relate to society’s expectations. The study delves into the story and seeks to illuminate from it, deeper meanings of female strength, female empowerment, female resilience, and how all these manifest- the obvious value of female autonomy when you are a female in a patriarchal world. The tales produce impressions on impressionable minds to help build and rebuild societal values over time. As a result, the study aims to capture the potential of classics such as Thumbelina in channeling complex imprints in readers and creating concerns in their minds when they choose to approach the gender identity challenge in literature and culture through these or other modes of research.