This paper is a product of my doctoral ethnographic study among the Kipsigis of Kenya. The research was conducted in Bomet, Kericho and Narok counties. The paper explores the underlying principles and contestations on the best interests principle and how scholars have recently located the best interests principle within legal pluralism. The paper then explores the foundation of Kipsigis customary law and the nature of childhood under the Kipsigis customary system. It also examines the pillars of the best interests principle under Kipsigis customary law such as; the promotion of a harmonious co-existence between the child and the family; guaranteeing the long term interest of the child; adhering to customary obligations of by the parents and a contextual understanding of what is in the child’s best interests. Using the underlying themes identified by scholars and reflected in various human rights instruments, the paper attempts to highlight the (in) consistency between statutory and customary conceptions of best interests and the role that customary law plays in protecting and anchoring the well-being of children.