Organ transplant recipients (OTR) are at a significantly increased risk for developing a wide variety of skin cancers, particularly epithelial skin cancer, Merkel cell carcinoma and Kaposi's sarcoma. Melanoma, skin adnexal neoplasm and cutaneous lymphomas are also more common in OTR and may differ in their clinicopathologic presentation from tumors in immunocompetent patients. The accuracy of clinical diagnosis of suspected premalignant and malignant skin lesions in OTR is modest. Therefore, histopathological diagnosis is an essential element for the diagnostic workup of skin cancers and, in addition, provides important information on prognosis. Squamous cell carcinoma and intraepithelial neoplasias (actinic keratosis, squamous cell carcinoma in situ or Bowen's disease) are the most common forms of skin cancer in OTR. The risk of Merkel cell carcinoma and Kaposi's sarcoma is dramatically increased in OTR. Merkel cell carcinoma shows a highly aggressive course. Kaposi's sarcoma tends to spread to extracutaneous sites. Primary cutaneous lymphomas developing after organ transplantation are rare. The spectrum of cutaneous B cell lymphomas in OTR, in particular, differs significantly from that of the general population, with a predominance of Epstein-Barr virus-driven posttransplant lymphoproliferative disorder. This review discusses the clinical and histopathological aspects of skin cancers in OTR, the impact of dermatopathological analysis on prognosis and the understanding of the pathogenesis of these neoplasms.