Shoes and socks. As mentioned before, wearing shoes and socks can contribute to the development of an ingrown toenail by crowding your toes. You can relieve the pain associated with an ingrown toenail and prevent the condition from worsening by wearing shoes, socks, and hosiery that fit snugly enough but still allows ample room for your toes. It may also benefit you to wear sandals as much as possible in lieu of shoes when you are suffering from an ingrown toenail. This will relieve pressure on the toenail.