"Now," Jon said. "How can we fix this? I wish you'd tell me."
The stone glowed and his grandmother was unable to keep from talking.
"Make a wish that if anyone leaves the confines of the town that they will be able to wear anything they want."
Jon thought it was a good idea. Maybe not the best, but good. The wish itself wouldn't contradict the 14th century clothing wish and it would allow the people of Jon's town to return to normal, given that they leave town, of course.
Deciding that it was the best wish to make, Jon made it and the stone glowed. And since his grandmother had no reason to be there anymore, she went back to where Jon's previous wish plucked her from.