Recent advances in artificial intelligence (AI) technology have led to increasing interest in the development of AI-based tool wear condition monitoring methods, heavily relying on large training samples. However, the high cost of tool wear experiment and the uncertainty of tool wear change in the machining process lead to the problems of sample missing and insufficiency in the model training stage, which seriously affects the identification accuracy of many AI models. In this paper, a novel identification method based on finite-element modeling (FEM) and the synthetic minority oversampling technique (SMOTE) is proposed to overcome the problem of sample missing and sample insufficiency. Firstly, a few tool wear monitoring experiments are carried out to obtain experimental samples with low cost. Then, a FEM model based on the Johnson−Cook constitutive model was established and verified according to the experimental samples. Based on the verified FEM model, the simulated missing sample in the experiments can be supplemented to compose a complete training set. Finally, the SMOTE is employed to expand the sample size to construct a perfect training set to train the SVM classification model. End milling tool wear monitoring experiments demonstrate that the proposed FEM-SMOTE method can obtain 98.7% identification accuracy, which is 30% higher than that based on experimental samples. The proposed method provides an effective approach for tool wear condition monitoring with low experimental cost.