This review aims to analyze the multiple factors affecting patients’ level of compliance (how much they wear removable devices/clear aligners) during orthodontic treatments and to investigate the available methods and devices to monitor the appliance wearing time and to improve it. A literature search was conducted on electronic databases (Pubmed, Scopus, and Google Scholar). The results of the present study suggest that compliance indicators may misestimate the intraoral wearing time. Compliance is affected by patient-related factors (age, personality traits, the importance of personal appearance, self-perception of malocclusion), appliance-related factors (visibility, pain/discomfort), and clinician-related factors (trust, clear and complete communication, motivation). The motivation of pre-pubertal patients is mostly external, while adolescents/young adults have intrinsic motivation for orthodontic treatment. Patients’ self-reports tend to overestimate the appliance wearing time. Even if there is a lack of evidence, teledentistry might improve patients’ awareness of being monitored, thus increasing the time for which orthodontic devices are worn. Compliance is a key factor for clear aligner treatments, but high-quality studies focusing on this aspect are missing. Further studies should focus on how to handle the lack of cooperation and how to increase compliance in order to maximize the treatment’s results.