Clustering data into similar characteristic groups is a commonly-used strategy in model development. However, the impact of data grouping strategies on modeling stem taper has not been well quantified. The objective of this study was to compare the prediction accuracy of different data grouping strategies. Specifically, a population-level model was compared to the models fitted with grouped data based on taxonomic rank, tree form and size. A total of 3678 trees were used in the analyses, which included six common species in upland hardwood forests of the southeastern U.S. Results showed that overall predictions are more accurate when building stem taper models at the species, species group or division level rather than at the population level. The prediction accuracy was not considerably improved between species-specific functions and models fitted with species-related groups for the four hardwood species examined. Grouping data by taxonomic rank provided more reliable predictions than height-to-diameter ratio (H–D ratio) or diameter at breast height (DBH). The form/size-related grouping methods (i.e., data grouped by H–D ratio or DBH) generally did not improve the prediction precision compared to a population-level model. In this study, the effect of sample size in model fitting showed a minimal impact on prediction accuracy. The methodology presented in this study provides a modeling strategy for mixed-species data, which will be of practical importance when data grouping is needed for developing stem taper models.