Injection of massive quantities of liquid silicone into body parts for cosmetic purposes is a popular practice among the transgender population. Although a myriad of short-term complications associated with this procedure have been described, few reports of chronic and persistent ailments exist. We present the case of a male-to-female transgender with recurrent necrotic leg ulcers associated with migration of the silicone material injected in the buttocks 25 years ago. We review the imaging findings as well as the clinical and pathological aspects of this presentation, with an emphasis on the necessity of a high degree of suspicion for silicone-associated complications in a transgender patient presenting with leg wounds. We highlight the importance of the characteristic sonographic snowstorm artefact generated by free silicone material in soft tissues in the diagnosis of this entity.