Rigid polyurethane foam, foam concrete, and vacuum insulation board are common roofing insulation materials. Their weathering performance under long-term multi-field coupling determines the overall service life of the roof. The weathering properties of rigid polyurethane foam, foam concrete and vacuum insulation panels were studied under freeze thaw, humid-heat, dry-wet, high-low temperature, and multi-field coupling cycles, respectively. The heat transfer and construction process of roof panels was simulated base on upper loading and moisture transfer factors. The result indicates that the mass loss of the foam concrete and the rigid polyurethane foam in the weathering test was significant, which led to the gradual increase of thermal conductivity. Meanwhile, the thermal conductivity and mass loss of vacuum insulation panels did not change due to the lack of penetration under external pressure, therefore, it is necessary to construct composite thermal–insulation materials to alleviate the adverse effects of the service environment on a single material and realize the complementary advantages and disadvantages of the two materials. The results of the numerical simulations indicated that the roof structure must be waterproofed, and its weatherproof performance index should be the same as that of the thermal insulation material. Considering structural deformation, the overall heat transfer performance of the product was increased by around 5%.