Air temperature in urban street canyons is increased due to the morphed urban geometry, increased surface area, decreased long wave radiation and evapo-transpiration, different thermo-physical properties of surface materials and anthropogenic heat which results in thermal discomfort. Outdoor thermal stress can be mitigated substantially by properly orienting the canyons. It is crucial for the urban planners and designers to orient street canyons optimally considering variable local climatic context. It is important especially for cities in warm humid climatic context as these cities receive higher insolation with higher relative humidity and low level macro wind flow. This paper examines influence of canyon orientation on outdoor thermal comfort and proposes the optimum canyon orientation for the Rajarhat Newtown, Kolkata – a city in warm humid climate zone. Different scenarios are generated with different orientations. Change in air temperature, wind speed, Mean Radiant Temperature (MRT) and Physiological Equivalent Temperature (PET) of different scenarios are compared to find out the optimum orientation by parametric simulation in ENVI_met. Analysing the simulation results it is observed that orientation angle between 30°–60° to north performs the best for the study area of the Rajarhat Newtown. The findings of this research will be helpful for the planners to orient the street canyons optimally for future development and extension of the Rajarhat Newtown, Kolkata.