A comfortable heel counter for a dress shoe is provided. The dress shoe includes an upper that has a first portion and a second portion. The first portion is connected to the second portion to define a heel counter pocket. A heel counter insert is disposed between the first portion and the second portion in the heel counter pocket. The heel counter insert is disposed in spaced relation to a calcaneus bone of a wearer. The heel counter insert provides comfort to the wearer and an improved fitting of the dress shoe.