Positive youth development (PYD) programs, as conceptualized by the 5Cs model of PYD where youth and emerging adolescents exhibit enhanced connection, confidence, character, competence, and caring, are operationalized through bidirectional individual-context relations to regulate development. However, in non-Western, educated, industrialized, rich, and democratic (non-WEIRD) cultures, the 5Cs outcomes may require alternative explication of the constructs in order to honor the culture in which positive qualities are formulated. Consequently, existing measures developed for a WEIRD context may be culturally irrelevant for non-WEIRD youth. The present study sought to develop a culturally valid measure of PYD through examining if the five factors associated with the theoretical 5Cs of PYD holds in a 78-item culturally adopted Caribbean measure of the 5Cs of PYD. Through exploratory, confirmatory, and moderated nonlinear factor analysis, the study evaluated the factor structure of the 78-item Caribbean measure, refined the scale though item and factor reduction techniques and investigated its within-culture measurement invariance and reliability. Data was collected from Jamaican NEET youth (N = 1116) with a mean age of 18.85 years (SD = 2.28). The study produced a culturally reflective, 4-factor 20-item Caribbean measure of PYD, which demonstrated moderate-high reliability, partial strict invariance across sex, and partial strong invariance across age. The findings supported a modified correlated factor structure for this scale and pointed to the need for further research in understanding the Caribbean conceptualization of the PYD factors of character and confidence, as the measure did not successfully capture these.