As palimpsests of multiple layers of historic, geo-political, and socio-economic complexity, contemporary cities demand innovative methods of deciphering and unraveling their development. Typically referred to as reading the city, these methods of delayering and synthesizing urban complexity have, for long, pre-occupied urban planners and decisionmakers. Drawing from its interdisciplinary literature, this paper explores a comprehensive model of reading the city. Using a qualitative approach from both the archival and visual data sources, this study provides a better understanding of complex layers of urbanism that guide urban planners, policy makers and decisionmakers in developing more convenient solutions to urban problems. With multiple layers of its urbanism, Istanbul makes a suitable case study for this purpose. Identifying three types of developments (controlled or top-down, partially controlled and outlawed, bottom-up), different interactive networks provide sufficient grounds for reading Istanbul. Reading these intricate layers of Istanbul's 'closed' and 'open' city (Sennett, 2017) in close proximity to a main transportation artery (D 100 highway) against the broader backdrop of its long history intertwined with geographic and socioeconomic push and pull forces provides a comprehensive tool for adopting similar methods for reading other cities.