Trichotillomania represents a chronic disorder in which patients traumatically remove their own hair in a bizarre pattern. Like obsessive-compulsive disorder, the hair-pulling behavior is recognized as senseless and undesirable, but is performed in response to several emotions and affects, such as increasing anxiety, or unconscious conflicts with a resultant tension relief. The condition may be episodic, but is usually chronic and difficult to treat. We present three cases of trichotillomania and review common clinical and pathologic findings of this, often chronic and socially debilitating, disorder. In addition, we discuss treatment options for dermatologists and how the collaboration with psychiatrists is the most effective management for these difficult-to-treat patients.