Research is needed to understand the effects that perfectionism may have in the occupational sector and whether its implications vary cross-nationally. In the current study the relationship of perfectionism on workaholism and work engagement was assessed through multiple groups structural equations models to compare strengths of association in the two countries after measurement invariance was examined for the measures in a sample of 804 U.S. and Italian participants. Evidence of similarities but also some differences were found between the countries. In particular, perfectionistic strivings was similarly related to workaholism in both the countries, whereas it was more strongly related to work engagement in Italy than in U.S. A statistically significant difference for work engagement (Italians more engaged that Americans) was also found, whereas no differences were found for workaholism. Cross-sectional nature of the study and culture used as a proxy is the main limitations. However, the cross-cultural approach adopted in the current study allowed us to report that evidence provided in a country might not be directly applied to another country, even if cultures are quite similar.