Living walls (LWs) are a climate change adaptation strategy for cities, as they have a cooling effect. Previous studies of the cooling effect of LWs were carried out in different climatic zones. These studies differed in their experimental design, or simulated data via models. Plants’ cooling capacity is explained by shading and transpiration, and depends on physical plant parameters, environmental factors, and system-related influences. A three-year-long trial was carried out between 2017 and 2019 at an experimental garden in Geisenheim, Germany. We chose a textile-based LW system with high water demand and plants from a wet/fresh habitat. We assumed that this would achieve high evaporative cooling. The experimental setup included four experimental walls, which were exposed to the north, south, east, and west, respectively. The plant choice was divided into three plant mix variants (Cascade, Ground cover, and Meadow) and a Control with no vegetation. We measured the temperature with sensors and a thermal imaging (IR) camera in different setups. The main results were that the measured vegetation temperature (TV) depends on air temperature (TA), measurement position, plant mix variant, and plant species. We could detect the cooling effect only at a small distance from the LW (microclimatic). Our methodological approaches should be continued in further studies.