This study tested a simulation workflow and evaluated design options for urban scale infill developments using environmental simulation tools. Options were evaluated for pedestrian thermal comfort in several design options for a tower in the park development in Toronto, Canada. Using Ladybug, ENVI-met, and Dragonfly, this simulation based-study compared existing, proposed, and optimized development options optimized for outdoor thermal comfortability. An agent-based simulation in Houdini was also used to consider how people might actually react and move in response to different zones of comfortability on the site. The study found that the preferred building massing on this site is either a podium high-rise or a mid-rise building with the highest density placed around the perimeter of a site. Testing both simulation workflows found that the Ladybug option is quicker and easier to use, making it more suitable for early stage design evaluation rather than ENVI-met. Future work should incorporate agent-based simulation in more detail, as it is only briefly explored as part of the workflows in this short paper.KeywordsThermal comfortSimulationEarly-stage design toolUniversal thermal climate index (UTCI)