The proposed paper presents an ongoing research project that focuses on re-defining the relationship between people and public space by bridging the physical environment with the digital realm. The project negotiates the parameters of this relation through an Augmented Reality tool that employs the technological features provided by enhanced reality glasses combined with a wearable computer and a wearable gesture-control device. The user has the ability to create virtual manifestations of a personal version of the surrounding urban environment and intervene digitally by painting, writing, posting and even designing within public space. The proposed AR tool provides users with the ability to creatively produce spatial 'tags' and comments upon a building's facade, a street's urban equipment, even within open spaces, helping them to release their imagination, express their own view about public space and shape a new type of spatial experience. Public space transforms into a canvas for personalized expressions of creativity and appropriations of the usual uncanny aspects of a city. The results of this interaction are artistic, architectural and/or social, but they primarily retain the personal view of the users' spatial perception. Aspects that are usually connected with private space are externalized, facilitating familiarity, initiative and fun. The aforementioned digital interventions can either remain personal or shared within a public cloud accessible by other users that forms a second layer of understanding the urban reality.