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This study describes a new approach to explore the design of public open spaces based on a multidimensional analysis useful to inform decision-making and foster the development of evidence-based architectural solutions. It presents an overview of the most relevant design variables and their constraints, providing, in this way, valuable information for the elaboration of a more sustainable urban design, considerate of the local socio-cultural values. This research aims at providing holistic guidance for the development of better design proposals in contemporary urban environments. More specifically, it seeks to synchronously characterize urban spaces at a multi-scale and multidimensional level, both quantitatively and qualitatively, by collecting contributions from Space Syntax Theory, Public Life Studies, Building Science and Environmental/Comfort Analysis in public open spaces. Many advanced digital tools are used for data management purposes and to generate and test iteratively different design proposals. The proposed methodology is based on a range of tests and analyses performed in the process of developing a new experimental project for Largo da Graça, an urban square located in Lisbon’s historic centre, which allowed the testing of different design solutions. This experiment generated a digital workflow for the design of the urban square, in which are registered all the steps undertaken to solve the many design problems identified by considering the efficiency targets (centrality, connectivity, enclosure, thermal comfort, security, social equity and interaction). The process comprises a sequence of comparative design reviews and records the choices made when dealing with latent information underlying changing conditions in the use of public space and the programmatic malleability of the Portuguese plaza. The description of the adopted design strategy and the examples extracted from the workflow are used to illustrate the practical approach of the proposed methodology. Ultimately, this study seeks to show how tightening the link between applied research and sustainable urban design can effectively support the design and planning of better public open spaces.