The rapid expansion of e-commerce has made the buying experience faster, potentially anonymous, and without limits of space and time. While this may produce benefits, for some individuals, online shopping can become an addiction. Therefore, the present study aimed to explore the psychological factors that may be associated with Compulsive Online Shopping, with a specific focus on the role of Attachment Styles and Family Functioning patterns as risk or protective factors. The study involved a sample of 306 participants (Mage = 31.86 years, SD = 11.925) who filled out an online survey consisting of the Compulsive Online Shopping Scale, Relationship Questionnaire, Family Adaptability and Cohesion Evaluation Scales-IV, as well as a demographic questionnaire. The results showed two significant parallel mediation models. In the first one, Secure Attachment was negatively and significantly related to Compulsive Online Shopping, with the mediation of Cohesion and Enmeshed Family Functioning. In the second one, Fearful Attachment was positively and significantly related to Compulsive Online Shopping, with the mediation of Cohesion and Enmeshed Family Functioning. Important implications for preventive activity and tailored interventions may emerge from these data.