Increased interest in urban thermal comfort has emerged in recent years with unpredictable weather patterns and unprecedented temperature extremes around the world. Urban modelling computer software can help with understanding interactions between built environment and microclimates. However, results of simulations can be difficult to interpret if acceptable thermal conditions for a location are unknown. Using a compound approach of field investigation and microclimate modelling for a pedestrian-only street in Toronto, Canada, this study investigates urban outdoor thermal comfort (OTC) in a cold continental climate. Four thermal indices were used to analyze field data and the results were compared with OTC research conducted in other climates. In this study, the Physiological Equivalent Temperature (PET) provided the strongest annual correlation with the pedestrian thermal sensation votes. A PET comfort range between 9°C and 24°C was found. Survey results were then used to interpret the simulated effect of urban vegetation within the case study microclimate during a summer scenario.