Cities are increasingly confronted with multiple environmental and climatic stressors. Especially during heatwaves, street canyons are both producers and sufferers of air pollution and urban heat island (UHI) effects, with severe risks on public health. To better design mitigation measures, it is important to consider both the microclimate behaviors as well as the perceptions of the local population. Therefore, this study examined pedestrian perceptions and microclimate modelings to understand outdoor thermal comfort conditions and air pollution dispersion in the case study neighborhood of Dortmund Marten, Germany. A field survey with measurement points at two street canyons for climatic variables and questionnaires on subjective thermal comfort and air pollution was conducted on a hot day during the heatwave period in August 2020. As a cost-effective method for modeling input generation, we extracted spatial and spectral data like albedo, roof materials and tree locations out of remote sensing imageries. Finally, we compared the modeling results of the physiological equivalent temperature (PET) index, particulate matter concentrations and air temperatures with empirical field measurement data and the questionnaire responses. Results indicate that during hot summer days with light winds from the east, the north-south orientated street canyon with tree arrangements tends to act as a tunnel for particulate matter accumulation. Coincidently, pedestrians show less thermal discomfort than calculated PET values in that particular area during morning and daytime, which underlines the dichotomy of such places. On the other hand, the low rise east-west orientated street canyon shows higher PET votes than predicted by the model. However, particulate matter concentrations were considerably underestimated by the model, while air temperature predictions provided meaningful results. The proposed workflow shows the potential to accelerate future preparations of input data for microclimate modelings, while the results can enhance wind-sensitive planning procedures and heat stress resilience in mid-latitude urban neighborhoods.