Improving urban walkability in the face of climate change is a critical challenge for urban designers. Street design strategies can mitigate heat stress and enhance pedestrian livability. Most previous studies conducted in hot climates recommend adopting deep canyons to improve summer conditions, overlooking the potential improvement of wide streets as essential structural elements of the urban fabric. This study was conducted in Biskra city, southern Algeria, where several mitigation strategies were applied to ‘Emir Abdelkader Boulevard’, as the main structural street inside the city, to create an optimal street model for arid climates. Five scenarios were developed based on three criteria: (Sc1) asymmetric profile northeast side (NES) > southwest side (SWS); (Sc2) asymmetric profile SWS > NES; (Sc3) cool paving; (Sc4) horizontal shading; and(Sc5) shading with a linear tree arrangement. ENVI-met software version 5.1.1 and the RayMan model were used to estimate the local climate conditions and outdoor thermal comfort levels based on the physiological equivalent temperature (PET). All scenarios reduced PET values across the street, with optimal reductions of −2.0 °C, −3.1 °C, −1.3 °C, −1.7 °C, and −1.2 °C in Sc1, Sc2, Sc3, Sc4, and Sc5, respectively. Concerning pedestrian areas, the optimal results durations were at the southwest side below the arcades’ sidewalks during peak hours: Sc2, Sc3, Sc4, Sc5 (2.2 °C–3 H, 2.3 °C–3 H, 2.4 °C–3 H, 2.5 °C–2 H). Sc1 performed best during daytime hours on the northeast side. The utilizing of these results can strongly help urban planners and landscape architects in creating climate-responsive streets that enhance citizens’ quality of life.