Almost all of the fashions from the middle ages seem odd by todays standards. I have no reason to believe that the hats in the pictures above had anything to do with horns or any other specific imagery. All the head wear from that period looks funny to me. Pointy shaped hats, however, were a common and freely chosen Jewish symbol long before there was any negative connotation attached to them, assuming that they ever did hold a real negative stigma. That form of dress seems to have fallen out of use by the fourteenth century.
You doubt that the pointed hat had a negative stigma? Please read more about it. How something is regarded today is relevant. Consider the swastika. I saw it on a soap tin at an antique shop and learned it used to be a symbol for purity. It really doesn't matter what it used to be. Today, the swastika is an unmistakable symbol of evil.