With 45# transformer oil as the base fluid, different concentrations of TiO2 nanomodified transformer oil were prepared via the thermal oscillation method. Nanomodified transformer oil with a concentration of 0.01 g/L was selected for evaluation via the breakdown test. Then, 0.01 g/L nanomodified transformer oil and ordinary 45# transformer oil were subjected to the variable control of different moisture contents and different temperatures, and breakdown tests under different types of electrodes were performed within the temperature range of −30 °C to 30 °C. The test results showed the following: Under severe cold conditions, the improvement effect of the breakdown voltage in different temperature ranges was different. Within the temperature range of −30 °C to −10 °C, the enhancement effect could reach 13% to 15%. Within the temperature range of −10 °C to 0 °C, the enhancement effect could reach 8% to 9%. Within the temperature range of 0 °C to 30 °C, the enhancement effect could reach 18% to 21%. Compared with the test results at high water contents, the improvement in the breakdown voltage amplitude of transformer oil by nanomaterials was more obvious at low water contents. In addition, nanomaterials could reduce the dispersion of the breakdown voltage to make the breakdown voltage more stable. Lastly, COMSOL was used to simulate the polarization process of nanoparticles under a uniform electric field and the influence of the trajectory of charged particles in the oil to further analyze the mechanism of the influence of nanoparticles in oil on the breakdown voltage of the oil gap. The simulation results showed that, when the particles were accelerated by the electric field, they moved irregularly. After adding nanoparticles, the charged particles were adsorbed by the nanoparticles when passing through the nanoparticles, which reduced the migration rate of charged particles in the oil. The breakdown voltage of the oil gap increased.