Traditional Benin dress and accessories constitute one of West Africa's most layered and historically significant systems of cultural expression. Each element of Benin dress - from the coral bead regalia of the Oba to the ceremonial wrappers of titled chiefs and the wedding attire of Benin brides - carries encoded meanings that communicate identity, authority, spirituality, and social hierarchy. The emergence of a vibrant commercial fashion industry in contemporary Nigeria has opened new possibilities for these cultural traditions, but has simultaneously introduced tensions around authenticity, symbolic misrepresentation, and cultural sustainability. Despite growing scholarship on African fashion and cultural heritage, limited attention has been given to how indigenous fashion enterprises in Nigeria negotiate the demands of commercialisation while sustaining cultural values and heritage, particularly within specific semiotic and historical contexts of the Benin Kingdom. This study addresses this gap by investigating the ways in which contemporary Benin-inspired fashion entrepreneurship negotiates the relationship between commercialisation and cultural sustainability from the perspective of Joy AG Fashion Style. Drawing on interview data, visual analysis, and relevant scholarship in African fashion and cultural studies, the article demonstrates that culturally grounded commercialisation can contribute positively to heritage sustainability when it is guided by cultural literacy, ethical commitment, and ongoing engagement with indigenous custodians. The study also identifies key challenges such as loss of symbolism, market pressure, imitation, and the high cost of authentic production that must be actively managed if commercial fashion is to promote rather than taint Benin cultural heritage. The article employs the Semiotics of Dress as its theoretical anchor, arguing that the commercial deployment of Benin cultural signs requires a semiotic responsibility that many current fashion actors have yet to fully demonstrate. The study recommends a more impactful collaboration among fashion entrepreneurs, cultural institutions, and policymakers to promote indigenous fashion practices, preserve cultural heritage, and support sustainable cultural entrepreneurship.