This chapter will be a valuable and timely contribution to the field of early years in its discussion of therapeutic approaches within early childhood, specifically Transitional Objects. Transitional Objects, including teddies, cloths, and tactile objects, will be discussed in relation to the children’s desire to have them close as a way of regulating their own emotions and wellbeing. Winnicott (Playing and reality. Basic Books, 1971) believed the connection to the Transitional Objects was the way they could link the inner and outer world of the child. The chapter will therefore consider how Transitional Objects can be understood within formal day care and how this can enrich experiences for children. The research methodology included in this chapter will be personal reflections of practice from an autoethnographic perspective. The theoretical and conceptual framework is informed by attachment theories and object relations, with the innovative contribution of this chapter being how Winnicott’s (Playing and reality. Basic Books, 1971) notions of Transitional Objects remain relevant within contemporary formal day care practice. In developing an understanding about Transitional Objects, the chapter focuses on children’s wellbeing and as a way of enabling them to flourish and fulfil their potential.