We have investigated the performance of silicone oil as an insulating medium with the aim of developing environmentally-friendly, flame-retardant electric power equipment. We have studied the streaming electrification characteristics of silicone oil during flow, with regard to its use in the cooling of electric power equipment, at temperatures from 30 to 130 °C. The effects of the insulator material on the charge density in the oil and on the accumulated charge density in the insulator were investigated. We use four kinds of insulators, including aramid paper, in these experiments. The silicone oil was negatively charged by streaming electrification, in contrast to conventional mineral oil. The magnitude of the accumulated charge density in the insulator was influenced by the kind of insulator. It was also found that the charge density in the silicone oil and the accumulated charge density in the insulator changed with increasing temperature. Moreover, we investigated the effect of the kinematic viscosity on the streaming electrification by performing experiments using oils with kinematic viscosities of 20 cSt and 50 cSt. We have considered the optimum combinations of silicone oil and insulator material.