A ring size measuring system to digitally measure a ring size of a user's finger including an image capturing device configured to capture a digital image of the user's finger, one or more processors, memory, and one or more programs, wherein the one or more programs are stored in the memory and configured to be executed by the one or more processors, the one or more programs including instructions for: receiving a digital image of a user's hand using the image capturing device, determining a distance between the image capturing device and the user's hand, and defining at least one-dimension point pair of a selected finger from the received digital image, wherein the one or more processors calculate a distance between the dimension point pair to calculate a diameter of the selected finger.