<p>This study examines the association between the big five “OCEAN” personality traits and late-life categorical spending regret. The categorical spending regrets examined are housing, food, clothing, appliances/furnishings, cars, leisure, child-related expenses, and providing financial help. Openness was associated negatively with spending regret on food. Conscientiousness was associated positively with spending regret on appliances/furnishings and cars. Extraversion was associated negatively with spending regret on food, cars, and providing financial help. Agreeableness was associated positively with spending regret on food, clothing, leisure, and providing financial help. The results for Neuroticism indicated no statistically significant association between the OCEAN personality traits and the categorical spending regrets tested. The findings provide insight into the psychological mechanisms underlying consumer spending regret and offer additional support for research on the psychological benefits of personality-matched spending.</p>