This study explored the classroom luminous environment with prism daylight redirecting fenestrations. The differences between the International Commission on Illumination standard sky and the Perez all-weather sky models were analysed. The study described the method of generating a valid bi-directional scattering distribution functions .xml data for the prism daylight redirecting fenestrations. A new evaluation metric, daylight evenness, was proposed to describe indoor illuminance dispersion. Radiance simulation results indicate that at various solar altitude angles, compared with conventional glazing, the micro-prism film and micro-prism with an added diffuse layer on clerestories can improve the space average illuminance levels 23.2% and 18.7% under the International Commission on Illumination sky, as well as 15.4% and 10.6% under the Perez sky, respectively. The analysis results indicate that prism daylight redirecting fenestrations clerestories can improve indoor illuminance uniformity and daylight evenness when the solar altitudes range from 23.8° to 75°. A method combined field questionnaire and high dynamic range image analysis were conducted for discomfort glare study. Adding a diffused layer to the prism film clerestory is expected to alleviate discomfort glare for east- and west-facing prism daylight redirecting fenestrations clerestory with the daylight glare probability reduction of 3.8% to 21.7% at various solar altitudes. The research results present promising advantages of applying prism daylight redirecting fenestrations at classroom clerestories to improve the daylight luminous environment.