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Outdoor heat stress is a growing problem in cities during hot weather. City planners and designers require more pedestrian-centered approaches to understand sidewalk microclimates. Radiation loading, as quantified by mean radiant temperature (TMRT), is a key factor driving poor thermal comfort. Street trees provide shade and consequently reduce pedestrian TMRT. However, placement of trees to optimize the cooling they provide is not yet well understood. We apply the newly-developed TUF-Pedestrian model to quantify the impacts of sidewalk tree coverage on pedestrian TMRT during summer for a lowrise neighbourhood in a midlatitude city. TUF-Pedestrian captures the detailed spatio-temporal variation of direct shading and directional longwave radiation loading on pedestrians resulting from tree shade. We conduct 190 multi-day simulations to assess a full range of sidewalk street tree coverages for five high heat exposure locations across four street orientations. We identify street directions that exhibit the largest TMRT reductions during the hottest periods of the day as a result of tree planting. Importantly, planting a shade tree on a street where none currently exist provides approximately 1.5–2 times as much radiative cooling to pedestrians as planting the same tree on a street where most of the sidewalk already benefits from tree shade. Thus, a relatively equal distribution of trees among sun-exposed pedestrian routes and sidewalks within a block or neighbourhood avoids mutual shading and therefore optimizes outdoor radiative heat reduction per tree during warm conditions. Ultimately, street tree planting should be a place-based decision and account for additional environmental and socio-political factors.