Based on the goodness-of-fit theory, the current research examined how parental socialization expectations and socialization practices in infancy predicted child social adjustment in the preschool year dependent on child characteristics in toddlerhood with a longitudinal sample of Chinese families. Participants were 272 Chinese mother-child dyads. Maternal socialization goals of child autonomy and obedience were assessed when the child was 6 months old. Maternal respect for autonomy and negative control were observed in free-plays at 15 months. Mothers reported child compliance and inhibitory control at 25 months and rated child externalizing behaviors at 37 months. Results showed that for children with low levels of compliance or high levels of inhibitory control, obedience socialization goals predicted more externalizing behaviors, whereas for children with high levels of compliance or low levels of inhibitory control, obedience socialization goals predicted fewer externalizing behaviors. Moreover, for children with high levels of inhibitory control, higher levels of respect for autonomy or lower levels of negative control foretold fewer externalizing behaviors. Conversely, for children with low levels of inhibitory control, lower levels of respect for autonomy or higher levels of negative control forecasted fewer externalizing behaviors. Together, our findings demonstrate that socialization expectations, socialization practices, and child characteristics are jointly predictive of social adjustment across early childhood and all the significant interactions are characterized by the pattern of a contrastive effect, therefore congruently supporting the goodness-of-fit hypotheses.