Trichoteiromania, a rare type of autodestructive hair damage, was first described 20 years ago. Despite the few cases described in the world literature, it can be assumed that there are many more patients with this disorder since it is not always diagnosed. The key aspects for the diagnosis are history data on episodes of regular rubbing of the scalp, the clinical features of trichoteiromania — one or more foci of broken hair in this area (sometimes along with the skin lichenification), as well as the trichoscopic pattern — broken hair 1–20 mm from the skin surface with the longitudinal splitting of their distal ends, which helps in differential diagnosis with other pseudoalopecies. The histological pattern of this disorder is nonspecific. Data on effective treatment methods for trichoteiromania are scarce; currently, there are no specific algorithms for its therapy. The treatment of trichoteiromania is a complex interdisciplinary challenge and typically involves a combination of psychopharmacological and psychotherapeutic approaches. We present two cases of patients with trichoteiromania treated in the St. Petersburg City Dermatovenerologic Dispensary and a literature review.