Moving into the realm of stereotypes, many Americans think of the pointed black hat as the key identifier of a witch. These folks are often the most surprised when they meet a real, modern witch wearing jeans and a T-shirt. But where did the stereotype of this pointy hat come from?
One thing to keep in mind in the search for this stereotype's origins is that it is peculiarly American and Western European, particularly from the British Isles, and it is a fairly modern invention. Witches in Eastern countries do not appear wearing pointy hats or any of the accoutrements that we commonly associate with the Halloween-style witch. Early woodcuts of witches in the Middle Ages showed them wearing scarves, or hats popular at the time, or even with their hair flying in the wind. Our media has popularized the view of witches with pointy hats as well as green skin, warts and brooms. I suspect the Wizard of Oz movie released at the dawning of the media age has more to do with the current stereotype of the "wicked witch" than does historical evidence!
The most positive interpretation I came across was echoed by Doreen Valiente as the probable source: Pointed hats were actually a visual representation of the Cone of Power that witches drew upon during their rituals. While this puts a nice, witch-friendly spin on the image, I find it to be rather unlikely. People in previous centuries who were creating woodcuts of witches tended to paint a very unkind picture and did not include positive aspects of true witchcraft as it existed at the time. Witches were portrayed dancing with devils and participating in all varieties of heinous rites, not drawing down the moon and healing the sick. It is unlikely that someone projecting a witch in such a light would bother to represent a Cone of Power, which is typically a positive force.
There is another, commonly held belief that the pointed hat originated with another persecuted group in Europe, the Jews. While Jews did wear pointed headgear, most scholars now believe these hats were not a likely source for the witch's pointed hat. After all, pointed hats were fairly common throughout the Middle Ages and Renaissance. This fact leads us to the source I find to be most believable, and m most mundane, for the Pointy Hat Look. During the late sixteenth and early seventeenth centuries, commoners in Wales and England often wore pointed hats. As fashions changed, the last to retain the old styles were the rural and peasant folk, who were considered "backward" by higher society and were usually the ones accused of heresy and witchcraft. Much as we today have stereotypes of the sort of student who might commit violence at a high school, so did the medieval people have their ideas of what sort of person might be a witch.
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