Multiple and counterstereotypic categorization of outgroup members reduces prejudice towards them. The present research addresses, for the first time, the role of political orientation in moderating the impact of these strategies on prejudice reduction. Given that right‐wingers have very likely a higher need for cognitive closure compared to left‐wingers and thus may be less tolerant to social diversity, for them, increasing the complexity of outgroup members through counterstereotypic versus stereotypic or multiple versus simple categorizations should be a less effective strategy of prejudice reduction than it is for left‐wingers and moderate individuals. Results using Romanians and immigrants as outgroup targets for Italian participants supported our prediction. Further, we found that the effect of prejudice reduction was explained by the sequential mediation of increased individuation of immigrants and reduced sense of threat from them. Implications of the interplay between multiple categorization and political orientation are discussed.