In the evolving landscape of design pedagogy, the exploration of social contexts has become imperative to address the dynamic nuances of cultural symbolism. This paper delves into the entangled web of traditions, gender identities, and societal perceptions, using the iconic Indian garment, the sari, as a focal point. Historically entrenched as an epitome of femininity, the sari’s association with women is deeply rooted in cultural, historical, and social contexts. However, the contemporary era witnessed a shift, where men expressed an interest in donning this elegant attire. This intriguing phenomenon prompts us to dissect the origins of the gendered association with saris, pinpointing when, why, and where this delineation occurred. The study critically examines the role of design educators in fostering a more inclusive design narrative. There are pertinent questions about how biases and conditioning are ingrained in our teaching methodologies, which often foster stereotypes. Design educators may unknowingly impart gendered perspectives to their students due to societal norms, hampering their creativity. The process of making design pedagogy gender-neutral requires educators to challenge traditional paradigms and embrace a fluid notion of identity. This requires a departure from rigid social contexts and a commitment to open dialogue, cross-cultural understanding, and acceptance of different gender expressions. The design pedagogy can truly break free from societal conditioning through unlearning, learning, and relearning, facilitating more equitable and diverse creative exchanges.