Onychomadesis occurs when the proximal nail plate becomes unattached to the underlying structures. When only one or a few nails are involved, the cause is usually physical trauma. A 23-year-old female presented with a 4-year history of recurrent onychomadesis involving her bilateral great toes that occurred during the springtime. While recurrent trauma from winter shoes or athletic activities may be a contributing factor, our patient was convinced that wearing tight-fitting socks during winter nights was the primary pathophysiologic process. By wearing socks only during the days and decreasing the amount of time the nails spent traumatized due to pressure, the patient's recurrent condition was eliminated.