Teledermatology, originating in 1995, has been one of the first telemedicine services to see the light of day. Two decades of teledermatology research is summarized in this review. A literature search was conducted in PubMed. Search terms included “teledermatology,” “teledermoscopy,” “tele wound care,” “telederm*,” “(dermatology OR dermoscopy OR wound care OR skin) AND (telemedicine OR ehealth or mhealth OR telecare OR teledermatology OR teledermoscopy).” Inclusion criteria were (i) Dutch or English written papers and (ii) publication year from 2011 to present or (iii) (systematic) reviews with publication year before 2011. One hundred fourteen publications and 14 (systematic) reviews were included for full text reading. Focus of this review is on the following outcomes: (i) actors (primary, secondary, tertiary), (ii) purposes (consultation, triage, follow-up, education) and subspecialties (tele-wound care, burn care, teledermoscopy (teledermatoscopy), teledermatopathology, and mobile teledermatology), (iii) delivery modalities and technologies (store and forward, real-time interactive, and hybrid modalities using web-based systems, email, mobile phones, tablets, or videoconferencing equipment), (iv) business models, (v) integration of teledermatology into national healthcare systems, (vi) preconditions and requirements for implementation (security, ethical issues, responsibility, reimbursement, user satisfaction, technique, and technology standards), and (vii) added value.To conclude, teledermatology is an efficient and effective healthcare service compared to in-person care. Teledermatology reduces patients’ travel time and waiting time, avoids (unnecessary) dermatologic visits, and improves access of care to underserved patients.