I think that he just wore the outfit on every yearbook picture day for forty years straight because it says that it all started in his second year teaching at the school when he realized that he had made the mistake of wearing the exact same outfit that he had been wearing in his picture from the year before. It also says that he was initially embarrassed and his wife dared him to make light of the situation and wear it again in the next year's pic and so it became a forty year-long running joke.. I agree though that the headline is somewhat misleading in how it is written because it does make it seem like the man wore the same outfit everyday straight for forty years.. I was thinking it must be like a Steve Jobs sort of thing where the guy just wore one particular thing all of the time but that he probably had several shirts that were all alike or something..