14th Century - Late Middle Ages

The Poulaine or crackowe were extremely long pointed shoes popularized in Poland during the late 14th Century and in the 15th Century. According to Wikipedia, Sometimes the point of the shoe would need support from a whalebone or a string tied to the leg (just below the knee) to stop the point getting in the way when they were walking. King Henry IV of England banned these extreme pointed shoes from being worn in the 16th Century and required all shoes to be a maximum of 2 inches long.

This image was adopted from: http://en.wikipedia.org/wiki/Poulaine