The current article compares the use of exploratory structural equation modeling (ESEM) as an alternative to confirmatory factor analytic (CFA) models in personality research. We compare model fit, factor distinctiveness, and criterion associations of factors derived from ESEM and CFA models. In Sample 1 (n = 336) participants completed the NEO-FFI, the Trait Emotional Intelligence Questionnaire–Short Form, and the Creative Domains Questionnaire. In Sample 2 (n = 425) participants completed the Big Five Inventory and the depression and anxiety scales of the General Health Questionnaire. ESEM models provided better fit than CFA models, but ESEM solutions did not uniformly meet cutoff criteria for model fit. Factor scores derived from ESEM and CFA models correlated highly (.91 to .99), suggesting the additional factor loadings within the ESEM model add little in defining latent factor content. Lastly, criterion associations of each personality factor in CFA and ESEM models were near identical in both inventories. We provide an example of how ESEM and CFA might be used together in improving personality assessment.