Based on early life experiences in which developmental, genetic, and environmental components interact, humans learn to trust themselves and others and connect emotionally in consistent ways that are broadly defined as “attachment styles.” These relatively stable patterns of interpersonal interaction are associated with either vulnerability to various health risks or resilience. Similarly, the mechanisms involved in sleep regulation undergo developmental changes that overlap temporally with attachment formation and remain sensitive to a series of biological, environmental and psychological influences. Interestingly, while sleep has been conceptualized as a fundamental attachment behavior given its dyadic context, few studies have explored its relationship with attachment style in various ages. We present the first systematic review of the published literature examining the relationship between attachment style and sleep in humans across the life span. While levels of evidence and methods of assessment vary significantly, the results suggest a possible life-long relationship between individual attachment style and sleep. These findings are particularly useful in understanding relatively ingrained psychological mechanisms that can affect and be affected by sleep. Clinical and research implications are discussed.