Analyses of entheseal changes (EC) in identified skeletal samples employ a common research strategy based on the comparison between occupations grouped on the basis of shared biomechanical and/or social characteristics. Results from this approach are often ambiguous, with some studies that point to differences in EC between occupational samples and others failing to provide evidence of behavioral effects on EC. Here we investigate patterns of EC among documented occupations by means of a multivariate analysis of robusticity scores in nine postcranial entheses from a large (N = 372) contemporary skeletal sample including specimens from one Italian and two Portuguese identified collections. Data on entheseal robusticity, analyzed by pooled sides as well by separated sides and levels of asymmetry, are converted in binary scores and then analyzed through nonlinear principal component analysis and hierarchical cluster analysis. Results of these analyses are then used for the classification of occupations. Differences between occupational classes are tested by MANOVA and pairwise Hotelling's test. Results evidence three classes which separate occupations related to farming, physically demanding but generalized occupation, and physically undemanding occupations, with the more consistent differences between the first and the last classes. Our results are consistent with differences in biomechanical behavior between the occupations included in each class, and point to the physical and social specificity of farming activities. On the other hand, our study exemplifies the usefulness of alternative analytical protocols for the investigation of EC, and the value of research designs devoid of a priori assumptions for the test of biocultural hypotheses.