This study evaluated Holland's (1997) theory of the equivalence of person and work environment structures by comparing the relationships among interest, ability, and skills based on individual and occupational ratings of constructs selected from the U.S. Department of Labor's O*NET database. Individual ratings by 816 college students were analyzed separately by gender. A bootstrapped property vector fitting technique was used to embed ability and skill constructs into a two-dimensional RIASEC interest circumplex. No significant gender differences were found in the integration of these constructs. There were differences between the person and environment models for 14 of the 32 (44%) abilities and skills. Discussion of the results focuses on implications for Holland's theory, occupational data, and measurement issues.