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With the increase of temperature, a tropical country like Singapore will face the challenge of mitigating the anthropogenic heat emissions and urban heat storage to maintain its quality of urban life. However, due to the complex nature of climate and urban fabric, it is difficult for urban planners to make climate-sensitive informed decisions on how to achieve better Outdoor Thermal Comfort (OTC) in an intuitive while holistic way. We develop a holistic and principled decision process via an implementation of a decision support tool which interactively visualizes how climatic factors, urban design scenarios, importance of spatial use, and various acceptability criteria impact the OTC assessment in a simple step-by-step manner. The advantage of this tool is that it serves as an agent-based climate-responsive urban design system that presupposes planner’s trust. A complete working example is provided which demonstrates how a user could choose the optimal scenario for a new public housing estate located at the northeast of Singapore.