Urban form plays a critical role when planning city transitions toward decarbonization. However, in urban climate conditions the complex relationship between urban form and cooling demand remains understudied. This thesis develops integrated approaches and knowledge in the transdisciplinary domain of urban morphology, urban climatology and energy-related fields while addressing the question: ‘How does urban form influence building cooling demand in urban microclimate conditions, and how can the magnitude of the relationship be assessed?’. By answering this main research question, the thesis delivers a threefold contribution. First, it contributes to the conceptualization and understanding of both the intrinsic and the extrinsic role of urban form, by identifying urban form characteristics that directly influence building cooling demand, and indirectly contribute to shaping urban microclimate conditions in buildings’ surroundings. Second, the thesis contributes to increasing the assessment accuracy of urban form-related climate and energy performance. It does so by developing a quantitative morphological method to identify Local Climate Types (LCTs) and by developing a modelling method that enhances the use of microclimate data as boundary conditions for energy demand assessments. Finally, for the city of Rotterdam, the testing of these novel methods provides an understanding of how and to what extent the form of buildings and contexts influence building cooling demand.