This study explores how rap and hip-hop artists construct a sense of “coolness” and engage in performativity within the cultural context of Kerala. By integrating both local and global influences, these artists establish unique fashion identities, which are analyzed through their Instagram profiles, YouTube videos, and live performances. Fashion, in this context, is conceptualized as a socio-cultural phenomenon shaped by multiple intersecting factors. Historically, films have played a significant role in shaping fashion trends in Kerala, a southern state of India. Cinematic representations have influenced public perceptions of clothing, grooming, and self-presentation, with audiences often emulating the attire and hairstyles of film protagonists. However, contemporary trends indicate a shift from cinema to digital platforms, particularly rap music videos and social media, as key sites for fashion discourse. These platforms facilitate intercultural and cross-cultural engagements, allowing artists to experiment with clothing, accessories, body modifications, hairstyles, and overall aesthetics. Unlike the conventional body representations often depicted in mainstream cinema, rappers and social media influencers introduce diverse fashion expressions that merge global and local stylistic elements. The fashion choices adopted by these artists are not merely aesthetic but also serve as markers of community, regional identity, religious affiliation, and caste dynamics. By embodying these varied influences, Kerala’s hip-hop artists contribute to the evolving discourse on identity, representation, and cultural hybridity in contemporary fashion.