Parents act as significant agents in determining whether or not their children are able to take risks. However, there has been little literature which explores the role of parental variables that predict parents’ decisions as well as which types of risky play they are willing to tolerate relative to their parenting styles. Therefore, the aim of this study was twofold. First, to examine the association of children’s risky play with the parental variables of gender, employment status, education level, place of residence (i.e., urban/rural), and age of children. Second, to examine the types of risky play parents tolerate relative to their individual parenting styles. Through convenience sampling, 302 parents were selected to complete two questionnaires, including the Risky Play Attitude Scale and the Scale of Parenting Styles. This study found that the employment status and educational level of parents as well as ages of their children positively influenced parents’ attitudes towards risky play. Parents who worked outside the home, and those with a university degree expressed a more positive attitude towards children engaging in risky play. Additionally, overprotective parenting was a critical predictor of risky play, particularly for both low-risk and high-risk play. Furthermore, there remains a need for further understanding of what triggers parental fears along with better equipping parents with the necessary knowledge and skills regarding risky play.