The “traditional” high street that was once a distinctive element in the city’s historic urban fabric, is now slowly declining. This decline is further intensified by the insensitive development of its nearby leftover lands and the lack of investment in the public realm. This research is meant to support a new interpretation for the contemporary high street in the basis of urban interstices and it aims to emphasize the importance of considering the high street and its community in the future city planning. For that reason, a number of urban and architectural placemaking interventions are studied, using a precedent analysis in order to explore possible urban regeneration strategies as an attempt to reconnect the high street to its surrounding urban fabric and functions. Eventually, through specific case of Shoreditch district, this paper seeks to establish the development capacity for the high street, in terms of the available development sites and their potential relationship with the existing infrastructure and services.