Drill wear detection and prognosis is one of the most important considerations in reducing the cost of rework and scrap and to optimize tool utilization in hole making industry. This study presents the development and implementation of two supervised vector quantization neural networks for estimating the flankland wear size of a twist drill. The two algorithms are; the learning vector quantization (LVQ) and the fuzzy learning vector quantization (FLVQ). The input features to the neural networks were extracted from the vibration signals using power spectral analysis and continuous wavelet transform techniques. Training and testing were performed under a variety of speeds and feeds in the dry drilling of steel plates. It was found that the FLVQ is more efficient in assessing the flank wear size than the LVQ. The experimental procedure for acquiring vibration data and extracting features in the time-frequency domain using the wavelet transform is detailed. Experimental results demonstrated that the proposed neural network algorithms were effective in estimating the size of the drill flank wear.