The upturned toe appeared around the time of the Hittites of Anatolia (c. 1500 B.C.) and appeared throughout Asia. In western Asia, the toe curled upward and was pointed; in eastern Asia, the toe curled upward but was generally shorter and rounder in shape than its western form. There is no known purpose for the curled toe, though it may originally have been a way of protecting the toes of the sandal-clad foot—extending the sole and curving it up in front of the toes.
During the twelfth century, the fashion of extending and curling the toes of the shoe reached amazing lengths in western Asia in the Ottoman Empire—especially among men. The longest known "Turkish" slipper measures some 30 inches from heel to toe; the Turkish slipper in the Peabody collections measures a mere 20 3/8 inches. Contact with the Middle East during the Crusades brought the fashion of pointed toes to Europe, but they didn't reach extreme lengths until the fourteenth century, when they were known as poulaines (right top) or crakowes (right bottom). Whether in eastern domains or in Europe, the length of the toe was a measure of the wearer's status. In England, the association with status was so firm and thought so important that toe length was governed by royal decree: kings and princes, 2.5 feet; nobles, 2 feet; knights, 18 inches, etc. Ladies' shoes were not quite so extravagant in length, perhaps because of the difficulty of pairing long skirts with long toes.
(Drawing from Sam S. Campion, Delightful History of the Ye Gentle Craft: An Illustrated History of Feet Costume. Northampton: Taylor and Son, 1876.)