The gradual tool wear is unavoidable in the machining process, it directly influences the surface integrity and dimensional tolerances of the components. The tool condition monitoring (TCM) systems have the capacity to make full use of the cutting potential of the cutting tools, which is of great significance for improving production efficiency and ensuring product quality. In milling titanium alloys, tool tipping is one of the main failure modes. Therefore, this study focuses on establishing a tool tipping monitoring approach for the milling process. The singularity analysis method based on wavelet transform was employed to characterize the variation of vibration waveforms quantitatively with the Holder Exponent (HE) index. The probability density distribution and statistical analysis were adopted to extract effective HE features from the HE indexes to correlate with the different tool conditions. The mutual information method was adopted to rank the discriminability of the HE statistical parameters. Then, several machine learning (ML) models were established with the screened HE features. Finally, the results of the experiments indicate that the Support Vector Machine (SVM) model has the highest classification accuracy and can provide practical guides on the tool changes.