During the high-feed milling process, the vibrations generated by interrupted cutting cause changes in the instantaneous tool posture, as well as in the working angle and the distribution of the thermal stress coupling fields of each tool blade. These changes result in significant differences in the wear distribution of each tool blade. In this research, well-designed experiments for the high-feed milling of titanium alloys were carried out to identify the key factors affecting the differential wear on the milling tool insert blades. A differential tool wear model for the tool blades was developed in order to comprehensively describe the effects of the location error of the blades, the vibrations in the tool posture, and the working angle of each tool blade. The wear status of the milling tool was simulated based on the dynamic tool trajectories and postures derived by the model, and the entire simulated wear distribution was investigated with an innovative wear boundary recognition method. The differential tool wear model was evaluated and validated by the milling experiments and further supported by simulations.