Any Yugioh player would buy the Gentleman's Hat to get Magical Hats to hide under!
I like it- it adds a nice little twist. Mabey also some places require you to wear a certain style hat- like a big gap you can jump across with the Frog Hat, or a block of ice only meltable with the Fire Arrow. Make it so people can only Enchant one hat at a time so people are forced to specialize?