The history of street space design is characterised by a series of planning paradigms that, based on the prevailing zeitgeist, assigned completely different uses and functions to streets. From approaches that regard streets as spaces that should be orchestrated in order to be visually pleasing, to those that are dominated by the aim of maximising profit by achieving the highest possible yield of developable land, to those that consider streets as traffic axes only, to the most recent ones that once again understand streets as spaces that are supposed to serve the people that use them. This paper provides a framework for a comprehensive understanding of street spaces by exploring these qualities. On the basis of an examination of a series of streets built at different times, the question is explored as to how different planning paradigms have influenced street design and how this is reflected in the actually spatial qualities observed today. Furthermore, a tool is being developed that enables a holistic understanding of street space. The SSSEIC-Tool consists of two different models: a theoretical concept and a computer-aided 3D model. The theoretical concept aims to comprehensively capture the various parameters that define the quality of the streetscape. To create this framework, interviews and a cooperative workshop were conducted with experts from practice, research and administration. The resulting concept presents a novel, holistic and systemic approach to documenting and analysing street space qualities, highlighting their interrelations and correlations. Building on this theoretical foundation, a 3D model was developed to visualise the relevant qualities and parameters in streetscapes. As a city information model (CIM), the model is also meant to highlight the influence and correlations of factors and thereby offer a viable planning framework for future inter- and transdisciplinary cooperation.