Istanbul, Turkey continues to transform and defy characterization as local, regional and global pressures bring about different kinds of responses to the built environment (Keyder: 1999, Clark: 2012). How, then, can we distinguish what parts of the city fabric, or which buildings are legitimately “traditional?” And, which of Istanbul’s building types signify vital urban architectural traditions that might also point to being legitimate new models for positively affecting the future of the city? This paper focuses on a building type that was first a 19th century import from the West, representing modern and cosmopolitan values (Benjamin: 1999, Geist: 1983). The arcade, or “passage” in Turkey, is an infill condition consisting of many shapes and scales and whose new exteriors and interior forms changed the ancient built surround. Today, approximately twenty-one varying passage structures constructed through the middle of the 20th century still exist in the center of the Beyoğlu district, mostly along the Istiklal Avenue. Beyoğlu‘s diverse, international, modern, and welcoming traditions, provide an intriguing background to suggest new socially-motivated architectural design (Gul: 2009) (Aksoy/Enlil: 2010). Research shows that the passage spaces with their unusual interior volumes and many floors that house the unique mixture of the district’s activities, have evolved to become iconic, respected monuments that express a combination of foreign and local vernacular and symbolize a kind of authentic vernacular. Yet, due to economic and political pressures in the city, changing ownerships, and evolving touristic interests, the multiplicity and freedoms have begun to break down and the passage building is succumbing to alterations, closure and disappearance, changing the street character and city movements (Author: 2011). Therefore, a hypothetical design project was developed to focus on the passage as a catalyst for rethinking and therefore legitimizing a new architectural infill for the present and future city, All of the solutions addressed current social and cultural needs in a globalizing city and world, and all activity programs incorporated new passage spaces to signify a means to sustain public freedoms. The street was addressed by inviting people inside to be a part of new possibilities for the arts, education and activism (Author: 2015). Thus expanding social relationships and encounters and suggesting an exploration of the utility and metaphorical associations of “passage in the city” a new legitimate urban vernacular is formed with respect of the past (de Certeau: 1984, Adanali: 2011, Soja: 2000).