One of the important influences on the child's upbringing, socialization and optimal development is the parenting style. Parenting styles are influenced by a variety of factors such as parental characteristics, child's characteristics, family and social context and the satisfaction with the quality of life and parental knowledge of the child’s upbringing as well. The aim of the study was to examine the relationship between the attachment, emotional stability and permissiveness in raising toddlers and preschool children and to determine whether there was a relationship between socio-demographic characteristics of parents and permissive parenting style in upbringing as well as which aspects of parenting (hostility, warmth, support, proactivity, reinforcement and physical control) were associated with permissive parenting styles in raising children. It started from the hypothesis that emotionally less stable parents, who are insecurely attached, would show more permissiveness in raising their child. 480 parents (N = 480) participated in the research and the instruments used were the General Data Questionnaire, the Attachment Questionnaire, the Multidimensional Parenting Questionnaire, the Emotional Stability Subscale from the Personality Examination Questionnaire (IPIP) and the Parenting Compliance Questionnaire created for the purpose of this research. The results showed that fathers were still more prone to permissiveness than mothers. The difference between mothers and fathers was found in all the positive aspects of parenting (proactivity, reinforcement, warmth, and support), and a significant difference was found in the preoccupied attachment. A significant connection between gender and preoccupied attachment, permissiveness, proactivity, reinforcement, warmth, and support were found as well. Based on all the results obtained, it was concluded that the parents who were less emotionally stable and who had assessed themselves as more preoccupied were more permissive in raising their child.