This study explores the rich spatial-cultural phenomena of street skateboarding and graffiti in Jakarta. The enduring appeal of both activities lies in their ability to inspire creativity, foster subcultural identities, and leave a lasting impact on culture. Through interviews and detailed observations by the first author, an active skateboarder, the research investigates the motivations, challenges, and cultural significance of skateboarding and graffiti. It examines their appropriation of urban spaces, exploring how they navigate local norms and regulations. The study also uncovers the social dynamics and subcultural communities that have emerged around these activities, shedding light on their role in shaping individual and collective identities within Jakarta’s urban fabric. The findings highlight the positive responses from the surrounding community, the strong attachment of the youths to their preferred locations, their constant adaptation and development of skills, and how they express their unique identities. © 2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group on behalf of the Architectural Institute of Japan, Architectural Institute of Korea and Architectural Society of China.