Freiberg disease, known as a Freiberg infraction, is an uncommon disorder of the second metatarsal head of the foot. Conservative treatment is recommended as initial management to relieve symptoms and minimize epiphyseal deformity. However, due to the rarity of this disorder, there have been few reports of long-term clinical and radiologic follow-ups of Freiberg disease treated with conservative treatment. We report Freiberg disease treated with conservative management including modification of shoe and insole. A 24-year-old woman presented with right forefoot pain. In plain radiography, the sunken appearance of the metatarsal head and periarticular spurring was observed. The articular cartilage was intact in magnetic resonance imaging (MRI), corresponding to Smillie’s stage 3 and Thompson’s type 2. We prescribed carbon fiber insert, customed semirigid insole with metatarsal dome and rocker-bottom shoe to relieve pressure under the metatarsal heads. Freiberg disease maintained a well-tolerable condition during 2-year follow-up period without further progression in MRI.