In this study we explore the variation in female breast shape across the younger (age: 18–45), non-obese (BMI < 30) North American Caucasian population, a population that has not previously been well-represented in studies of breast shape. A method of classifying breast shape was developed based on multiple data-mining techniques. Forty-one relative measurements (i.e., ratios and angles) were constructed from 66 raw measurements (circumferences, depths, widths, etc.), extracted from 478 CAESAR (Civilian American and European Surface Anthropometry Resource) scans, using self-developed Matlab® programs. Seventy subjects were regarded as outliers and were removed. The remaining data were transformed and standardized to ensure robust analysis. To judge results, an algorithm was developed to visualize clustering outcomes in the form of side profiles of breasts. The results of three clustering methods, namely hierarchical, K-means, and K-medoids clustering, were compared. Finally, breast shapes were categorized into three and five groups by two different cluster number selection criteria proposed by the study: (1) based on misclassification rate; (2) based on the goodness-of-fit of the model. Several of the relative body measurements were identified to be critical in defining breast shape. The findings and the proposed methods of this study can contribute to the development of improved shape and sizing systems of bra products that work for both manufacturers and consumers. The new methodology developed in this study can also be applied to other types of intimate apparel products where an understanding of body shape plays a key role in body support, comfort, and fit.