An experimental study was conducted using the tracking wheel test (IEC 62217) method for evaluating the performance of insulator materials, in particular ethylene propylene diene monomer (EPDM) and silicone rubber. In addition, we studied the tracking characteristics resulting from applying the same method for the shape of the insulator housing, that is, the performance of regular and alternating sheds. The evaluation parameters were leakage current, surface characteristics, SEM, EDX, hydrophobicity, and temperature distribution; likewise, we applied the commercial frequency dry (and wet) flashover voltage test. We found that the regular shed had a greater leakage current than the alternating shed and that the recovery of the hydrophobicity in terms of rest time was greater than that of the EPDM in terms of leakage current. All of the regular-shed insulators of silicone rubber had tracking traces and choking on the sheath parting line, while the alternating shed showed only choking at the interface but no tracking traces. Therefore, it can be concluded that the commercial frequency wet flashover voltage of the silicone rubber with regular shed before and after the tracking wheel test is higher than that of the alternating shed.