Retro-reflective (RR) materials are largely included among the strategies to mitigate Urban Heat Island (UHI) phenomenon in the urban spaces thanks to their optical directional properties. As materials potentially used in the building exterior envelope, RR materials are subjected to outdoor aging and soiling processes, which could alter their optical behaviour. In this perspective, the investigation focuses on the characterization of the optical performance of several types of RR plaster coatings after outdoor aging and soiling processes. The RR plaster coatings were previously developed and studied, before undergoing the outdoor exposure. The RR samples were developed covering the support with a reflective white paint and glass beads. Five different microsphere diameter ranges and three different microsphere superficial density ranges have been employed. In this paper, the RR plaster coatings were tested in terms of optical properties after outdoor aging and soiling and results were compared with data of the same plaster coatings pre-aging. Generally, all RR aged samples show a lower solar reflectance in the Vis region with respect to the pre-aging conditions. The RR behaviour is qualitatively maintained after aging and soiling. The RR sample made of glass beads of 200–300 μm diameter range could represent the best solution both in pre- and post-conditions and both in terms of solar reflectance and retro-reflective behaviour, regardless of the density of microspheres used.