Infiltrating lipomatosis of the face is a very rare entity which is characterized by the collection of non-encapsulated mature adipocytes infiltrating local tissues, resulting in craniofacial deformities. Psychomotor development of the patients is normal, esthetics often being the primary concern to seek treatment. The presentation is always unilateral with hypertrophy of hard and soft structures on the affected side of the face. The pathogenesis of the condition is unclear. This condition shows a wide phenotypic range, uncertain prognosis with high rates of recurrence after surgery, and variable post-op cosmetic improvement. The condition shows no gender predilection, with most of the cases presenting in and beyond the second decade of life. Here, we present a series of four cases presenting in varying age groups with history of recurrence in three cases.