I agree. There are some men who simply do not want to dress like an adult. I have seen the same thing others here have seen. A father and his teen-age son dressed almost exactly alike. The father dressed like his teen-age son, that is. Rebellion may have started it at first, but then rebellion becomes the norm. Their desire to be different has backfired. These people have to choose...either decide to look like an adult and accept the fact that a 50 year old man in baggy jeans, ball cap turned backward with large shirt untucked looks ridiculous or keep re-inventing themselves every time pop culture deems it necessary.
Usually the older fellows dress a bit too young. However this discussion made me think of the Alex Keaton character from Family Ties. He rebelled against his parents (who were former hippies). Alex was in high school and he typically wore ties, suits, slacks and sport coats. So if you want your kids to dress up, you should dress down a bit.