In this study we investigated the role of personality for wellbeing in the retirement transition. In a sample of Swedish older adults (N = 2.797) around retirement age (60–66), included in the Health, Aging and Retirement Transitions in Sweden (HEARTS) study, we tested if personality types and/or traits moderated the effect of retirement on change in subjective well-being across one year. We identified four personality types in a latent profile analysis. Using latent change score models, we found that those who retired between assessments showed stronger increases in subjective well-being compared to those not retiring. For one group with low openness, agreeableness, extraversion and conscientiousness, but high neuroticism, retirement was associated with a decrease in well-being. When only personality traits were included, we found a moderating effect of agreeableness so that high scores on agreeableness enhanced the increases in well-being after retirement. The results are compared and discussed in the light of research on personality and retirement.