Pointed shoes as we know them today began from much different circumstances...and appearances.
The trend towards pointed shoes originated somewhere around the 12th century. The earliest known invention of pointed shoes was in France (made for the Count of Anjou in order to mask his deformed feet). Later in the 12th century King Phillip Augustus didn't want to look lesser to the common folk, so he declared that his subjects' points should be between six and twelve inches long based on their status. It was also said that King Henry II of England had deformed feet, bringing about his wearing of narrow, pointed shoes. During this time period, the Knights of Richard the Lionhearted start wearing "sollerets", a downward curved pointed toe shoe, so their feet wouldn't slip out of their stirrups. Some historians also attribute this trend to the Crusades as well as exposure to Eastern styles of dress. It should be noted here that these shoes were worn by men and not women.
This image is dated in the 12th century. It is a painting of Philip Augustus and Richard the Lionhearted (his uncle) in full regalia (notice the pointed shoes) right before taking off for the Third Crusade.
By the 14th century, the pointed shoes became so popular that people competed to see how long their points could be: the longer the better. The length of the points became a mark of nobility and eventually the points were so long some people had to secure them at the knee. Clergy men complained that they couldn't kneel to pray with such points, people started tripping, and soon enough laws enacting pointed toe length came into play. With the popularity of these pointed shoes, also called "poulaines" or "crackowes" (as they became popular in Crackow, Poland) shoes, also came the disgrace as some men would wiggle their points suggestively as an attractive woman walked by. This led to "poulaines" being viewed as vulgar.
1460 was the pinnacle of the pointed shoe, when Edward IV created a law prohibiting certain length extensions for "commoners."
A few years later, the trend began to wane, mainly due to two events that happened:
1. Duke Leopold II of Austria died after he tripped over his long, pointy shoes while trying to escape his assassins.
2. King Charles VIII of France had deformed feet (what is it with royalty and deformed feet?) which required that the shoe he wore be a square toe, thus again changing the fashion for the ruling class.
Here is a piece of art from the time, depicting the current popular look of pointed shoes for males:
"L'instruction d'un jeune prince (Instruction of a Young Prince)", an advice book on good conduct by Guillebert de Lannoy, c. 1468-70
15th century "poulaines"
After 1500 a blunt, pointed toe returned (this is also the time that heels emerged) and by the 17th century women decided that a pointed toe is much more feminine and thus we start to see the trend cross over genders. However the fabrics used during this time were extremely dainty and stayed that way up until the 19th century. Men also began to wear pointed toes again, but this time in a minimalist way.
19th century pointed toes (designer uncredited), symmetrical soles
In 1955, Marilyn Monroe emerged and created a demand for the tall stiletto heels with extremely pointed toes (created at this time in Italy and dubbed "winkle pickers"). This then became the model for today's pointed heel/shoe.
A Lennards ad for pointed shoes with a heel, c. 1950s.
From the 1950s to today the pointed shoe has been a staple in female wardrobes across the world. The colors, heights, fabrics and circumstance may change, but the point remains in vogue, a staple if you will.
Christian Louboutin pumps, Spring 2009, Saks Fifth Avenue catalogue