In hot, semi-arid zones, cities are experiencing longer and more intense warm spells. Although the literature offers strategies to mitigate this threat, studies verifying their feasibility are limited. In this study, we aim to ascertain the feasibility of reducing land surface temperature (LST) through greening. We combine LST analysis with a feasibility assessment of cooling measures and consider physical and ownership dimensions alongside environmental and social factors, with Ouagadougou (Burkina Faso) serving as a case study. The average LST during the hottest period (April–May) was calculated from ECOSTRESS and Landsat remotely sensed data, and multiple regression models were used to analyse the relationship between LST and land cover/land use across the city’s districts and sectors. Our assessment incorporates greening scenarios, SWOT analyses, and equity assessments, and our results indicate that barren land is the primary determinant of diurnal LST. Planting 0.45 million trees could reduce LST by up to 2.4 °C in peripheral sectors if large roads, utilities, and vacant lands are targeted. This may reduce disparities in tree cover between sectors but could widen the gap between districts. Recommendations include a more hierarchical street network, enhancing utility provision, and reducing barren land in the peripheral sectors.