This study aims to examine the ability to flexibly enhance and suppress emotional expression, known as expressive flexibility, in relation to physical and psychological health, as well as trait emotional intelligence (EI). A sample of 503 Italian (M_age = 28.65 ± 9.26 years, 85.1% females) participants completed the Italian version of Flexible Regulation of Emotional Expression (FREE) Scale, the TEIQue-SF, and the Short Form-12 Health Survey. Confirmatory factor analysis indicated that the Italian version of FREE showed adequate psychometric properties. In both genders, results of correlational analyses indicated that enhancement ability was associated with well-being, emotionality, and sociability, whereas suppression ability was associated with self-control. Regression analyses, controlling for age and gender, indicated that suppression and inversely enhancement abilities, predicted the perceived psychological but not physical health. Well-being, self-control, and sociability also contributed to explaining variance in the model. The interaction effect of enhancement and suppression was not significantly associated with either physical or psychological health. Overall, these results suggest that enhancement and suppression abilities differentially contribute to psychological health when trait EI is accounted for. Clinical implications and future directions for research on expressive flexibility are discussed.