The flashover performance of insulators is the foundation of the calculation of precise lightning protection. The material and structure of an insulator affect its flashover performance but the research on the differences in the flashover performance of different insulators and the analysis of the reason for these differences have not been clear. In this paper, lightning impulse flashover tests of two types of insulators (composite and glass insulators) were carried out in the National Engineering Laboratory (Kunming) for Ultrahigh-voltage Engineering Technology. In these tests, the insulators were hung in a 110 kV double-circuit transmission tower and a standard lightning impulse (1.2/50 μs) was applied to the insulators. The discharge path and the 50% impulse flashover voltage of the insulators were recorded. At the same time, the electric fields in the vicinity of different insulators were calculated using the finite element method with COMSOL Multiphysics. The electric field distribution and the uneven coefficient were analyzed. Combined with the flashover test data and the electric field simulation, the relationship between the flashover performance (discharge path and 50% impulse flashover voltage) and the electric field (electric field distribution and uneven coefficient) is found. The simulation results are in accordance with the test data and the conclusions can provide useful references for the external insulation design of transmission lines and the optimization of insulators.