Our direct environment affects our lives directly. Christopher Alexander saw that we are able to feel or see if an object or structure is natural through the characteristics of them. He also saw that we generally feel better near these living, natural structures as it more closely resembles ourselves. Our bodies and our surroundings are made up of far more smaller than large things. When structures follow this pattern they are considered to be more natural, and when they move away from this pattern they are considered to be less natural and thus often boring or ugly. This scaling law is used to analyse the complex networks within cities. By analysing underlying structures instead of direct geometry it becomes possible to identify how living they are.This study applies these theories to analyse urban morphology within different cities. By identifying living structure within cities comparisons can be made between different types of cities. Specifically artificial and historical cities are analysed as they are counterparts in livingness. Following the identification of the living structure within these different types of cities an assessment can be made on what kind of an effect this has on our wellbeing based on Alexander’s theory. To see how living structure evolves over time a second analysis is performed which compares a city with its own evolution through time.Firstly natural cities and natural streets are identified in a bottom up approach based on the underlying structures of OpenStreetMap road data. Thereafter historical cities are compared with artificial cities because historical cities generally have living structure while artificial cities lack this. Then the developments of a historic city are identified and compared temporally. This research finds that current usage of concrete, steel and glass combined with very fast development speeds is detrimental to living structure within cities currently. Newer city developments should be performed in symbiosis with older city structures and the structure of the development should inhibit scaling as well as the buildings themselves. It is not sufficient to look only at geometry when managing cities, the importance of the fractal geometry, which is initially invisible must not be underestimated.