This research discusses designing an experimental framework to reinterpret the urban form of self-organizing traditional Islamic cities with computational design tools. These types of ancient urban tissues are characterized with emergent behaviour that is expressed through the incorporation, in their spatial structure, of apparent randomness and inherent complex organization. The said framework highlights some of the important physiological and organisational features of theses urban environments before reinterpreting to be incorporated in a computational design process. A set of functional constraints and objectives inspired by characteristics of the aforementioned urban settings are defined for a form-generation algorithm. This methodology is described through a threefold process comprising of formulation, generation and evaluation steps that allow for the optimization of the urban form. While making use of algorithmic design software to define the components for a generative urban design model, this research also uses multi-objective optimization evolutionary algorithms as a theoretical basis for the optimization and analysis of this model. An evolutionary computing solver and Pareto front evaluation methodology are used in order to evaluate and visualize a multitude of optimized solutions. Built on these features, the development of an experimental urban model means both to explore the generation of proposed results and to develop the design system behind it.