Skopje underwent many changes to its urban environment, caused by different factors both human and natural. Due to these impacts the community’s responses have ranged from deeply personal to collective mobilization of attachment that erupted during some periods of rapid change. After the big changes that occurred after the 1963 earthquake and the dissolution of Yugoslavia when Macedonia reached its independence, the city and its citizens continuously struggled to find urban identity that could reflects the collective memories of the previous times. In searching for this urban identity, the last phase of the process was the “Skopje 2014” agenda promoted by the then ruling government. This paper presents the transitions in Skopje’s urban panorama. It analyses and presents how such transformations of urban and architectural environment can affect the urban identity and the collective urban memories.