107. Man IN or WITH a hat?

The question is about the preposition. The boy with big eyes is my friend. --> with The boy in a black vest is my friend. --> in What's the different between "with" and "in" in the two sentences? How about "a scarf", "black shoes", and "earrings"? Which preposition is right? This question has been discussed so much and I don't see any rules or guidelines in my resources, so I am mostly going by ear on this one. If anyone cares to add enlightenment, feel free. Many times the prepositions are exchangeable, and in other instances they aren't. For instance, we say the man with the hat, but Dr. Seuss also says the man in the hat. But generally, (except for hat, glasses, or shoes which use both in and with) it seems smaller accessory things use only with, like watches, scarves, earrings, and gloves. And I would say with big eyes. If you say the man with the vest, it might sound like he is carrying it instead of wearing it, but I think it is acceptable and more common to say the man with or in the vest to mean that he is wearing it. This probably applies to most big articles of clothing.