While patterns of adolescent personality development are country-specific, previous studies that have examined them have been limited to the Netherlands and Finland. This study aimed to identify the patterns of personality development and examine the relationship between these patterns and psychosocial functioning among Japanese adolescents. Overall, 618 Japanese adolescents (49.5% girls; 16 years) participated in the annual longitudinal survey from 2013 to 2016. Using latent class growth analysis, the following four patterns of personality development were identified: resilient, over-controlled, vulnerable, and moderate. Although the mean-level changes in the Big Five domains were generally insignificant among the four patterns, the vulnerable pattern showed a progressive increase in conscientiousness, and the moderate pattern showed a decrease in neuroticism and an increase in conscientiousness. Furthermore, multivariate analysis of variance tests indicated that the resilient pattern showed higher subjective well-being and lower psychosocial problems than the other personality patterns; the over-controlled pattern showed higher internalizing problems than the resilient pattern; the vulnerable pattern showed lower subjective well-being and higher internalizing problems than the other patterns; and the moderate pattern scored between the resilient, over-controlled, and vulnerable patterns in both subjective well-being and psychosocial problems. These findings suggest that the vulnerable and moderate patterns, which are immature patterns compared to the resilient and over-controlled ones, showed positive changes to the direction of maturity from middle to late adolescence in Japan.