World's Oldest Shoe - Recently the expert found the shoe which is made up of leather. The 5,500 year-old shoe was discovered by a team of archaeologists in a cave in the Vayotz Dzor province of Armenia, on the Iranian and Turkish borders. It is the right foot shoe and had been stuffed with grass. The shoe is the oldest piece of leather footwear in the world, a fact that came as a shock to the discoverers.