The paper concerns the monitoring of the tool condition on the basis of vibration acceleration signals. The cutting edge condition is determined by wear on the flank surface of the drill. As tools, a twist drills made of cemented carbide were used. A gray cast iron plate EN-GJL-250 was used as the workpiece. Based on the signals, appropriate measures correlated with the wear of the drill were developed. By using binary decision trees CART (Classification and Regression Tree) with two data partitioning methods (Gini index and Cross-entropy), the original number of measures was limited to the most common and those that provide the smallest error in the tool condition classification. Comparing the results for the best trees built with different measures of partition quality in nodes for all available data indicated a better performance of the Gini index. The applied solution allows for high accuracy of the tool classification. The solution is to be used in industry.