This research explores the concept of imageability, emphasizing its crucial role in shaping the attractiveness, recognizability, and memorability of urban spaces, defining the character and identity of cities. The study recognizes the contemporary challenge posed by rapid urban development, which often leads to the loss of historical fabric, design language, and local cultural life. This, in turn, erodes the image of cities over time. This research represents how we see ourselves and how we see the world with time. The research's main objective is to investigate elements that contribute to a place's attractiveness as a key aspect of imageability. The focus is on identifying the spaces, elements, color, or symbols which help visitors and inhabitants to remember a particular city in its significant style of architecture and design, which make each city different from one another. These elements collectively play a pivotal role in exploring visual imagination and design semantics. The study employs a research-through-design approach using a probe consisting of 11 cards to explore imageability. This methodology allows for detailed data collection on how participants visualize and interpret different images. By analyzing the impact of semantic cues on image recognition and recall, this research aims to contribute to a deeper understanding of how visual imagination shapes human perception. The findings are expected to offer insights into the processes underlying imageability and the role of visual imagination and semantic cueing in urban identity formation and its application in urban design and heritage conservation.