Also, aren't wizards with big pointy hats just a little too silly at this point? They were fine with Daggerfall, but I like to think the series has gotten a bit too serious for that type of hat.
i think if implamented properly, they can pull it off. obviously not making an extremely pointed hat, but something that feels like it could be in TES.
the evil look of hoods is due to to colour and width at the neck. These are what make the sith look much more evil than jedi. http://gruntfarter.co.uk/wp-content/uploads/2010/10/darth-sidious-5325.jpg vs http://images.wikia.com/swfanon/images/6/64/Obi-Wan_Kenobi_(IS).jpg hoods
and the hood of my avatar adds to his evil dark assassin look
What about tam o shanters or some broadbrimmed felt hats? You rarely see those in fantasy games, but they would still look appropriate in a medieval setting i think.