Teledermatology has become very popular, and not only due to the SARS-CoV-2 pandemic. Patients with occupational skin diseases (OSDs) could also benefit from teledermatology services as part of their follow-up care, but the opportunities and challenges for patients and dermatologists, especially regarding quality and satisfaction, need exploration. In this single-center feasibility study, 215 patients taking part in a tertiary prevention program for OSD were invited to participate. After obtaining consent, a follow-up video consultation appointment with the center’s dermatologists was made. Quality and satisfaction with the consultations were evaluated by fully standardized online questionnaires filled in by the patients and dermatologists. A total of 68 teledermatological follow-up consultations were conducted by 10 dermatologists on 42 patients. Half of the dermatologists (50.0%) and 87.6% of the patients were satisfied with the video consultations. However, the lack of physical examination seems to be a problem, especially from the physicians’ point of view (75.8%). A total of 66.1% of the dermatologists and 87.5% of the patients saw video consultations as useful supplements to face-to-face consultations. The results of our feasibility study indicate general satisfaction of patients and physicians with teledermatological sessions in occupational dermatology, especially as a useful supplement to face-to-face consultation.