The fashion industry has received harsh criticism about its increasing environmental footprint. As a result, formal clothing swapping has evolved into collaborative sharing practices, sometimes leading to circular social and economic developments. In either case, it transforms how individuals behave around possessing and sharing clothes for what it can bring to them and their collective well‐being. This study explores what factors (e.g., economic, hedonic, environmental, and activism) motivate individuals to swap their clothes and why culture may be an important moderating factor to consider. An online Amazon Mechanical Turk (MTurk) survey comprised of the NextGen (individuals between 18 and 35), 51.6% of workers, and 28% of students (n = 279) from various countries analyzed through ANOVA regressions led to clear evidence of the moderating effects of culture on motivating factors in swapping behavior for clothes: (1) economic motives are stronger in masculine cultures; (2) hedonic motives are stronger in collectivist cultures; (3) environmental motives are stronger in collectivist, low power distance, and indulgent cultures; (4) activist motives are relatively strong in collectivist, feminine, low power distance, low uncertainty avoidance, and indulgent cultures; (5) the collectivist culture had a moderated influence due to hedonic, environmental, and activist motives as in this culture, greater mental emotions may be aroused. This study highlights economic and hedonist motives as influential variables that correspond to more actual consumer needs. Results also indicate specificities on NextGen culture identity and motivations to push forward a shift in up‐swapping systems, engaging decision‐makers for more transparent, sustainable efforts.