I was sorting through my closet and came upon a pair of shoes I bought a few years ago. The toes are so pointy I have never worn them. They are just too uncomfortable. I suppose it could have been worse. This could be the fourteenth century.

Crusaders returning from the holy lands flaunted a new shoe style for men that featured curled-back, pointy toes (known as poulaines). In the 14th and 15th centuries the fashion evolved. Toes grew and grew until some men sported points two feet long that had to be tied to their garters. These points made it hard to walk without tripping.

A steel version of the pointy toed fashion was even worn by knights. During the Battle of Sempach in 1386, knights were forced to break off the points of their shoes before leaping from their horses to battle on the ground.*

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*Source: Schnurnberger, Let There Be Clothes, page 135