In the realm of rotary machine maintenance, rolling bearings emerge as crucial yet frequently vulnerable components. Ensuring their operational integrity is pivotal for the overall safety and performance of the machinery. Traditional diagnostic methods have utilized a variety of signal processing techniques, ranging from blind source separation to wavelet analysis, and more recently, deep neural networks (DNNs). However, a significant challenge in this domain is the scarcity of labeled failure data in real-world applications, leading to a reliance on data augmentation (DA) techniques to enhance the quality and quantity of the training data. Compounding this problem is the use of DA techniques tailored for images, which are not suitable for the time–frequency representations. This study proposes an innovative Data Augmentation with Analytic Wavelets (DAAW) approach, tailored specifically for time-series (TS) data classification in bearing fault diagnosis. The essence of DAAW lies in its ability to generate synthetic scalogram samples that closely mirror the properties of original samples. The proposed DAAW is directly applied at the input stage of a learning model by successively adjusting predefined parameters to generate scalograms, without the need for auxiliary DA algorithms. This technique is versatile in generating synthetic time–frequency data samples, and the parameterization enables it to be tailored to different time series datasets. Through experimentation with publicly available datasets, we show that combining a simple Convolutional Neural Network (CNN) with the proposed approach results in improved performance. It outperforms existing methods, achieving a mean classification accuracy of 99.49%. The critical distance for average accuracy, as determined by the Nemenyi post-hoc test, is 0.4619. Our results also show enhanced performance with accuracy rates of 90.14%, 78.94%, and 62.86% even under low signal-to-noise ratio (SNR) conditions, using 80%, 60%, and 50% of the dataset, respectively, for model training. Notably, its efficacy remains robust even under challenging low SNR conditions. The proposed DAAW significantly improves classification accuracy in bearing fault diagnosis, simultaneously obviating the need for proxy DA tasks.