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ClintTom, there are ways to date Wilson hats like the Robinson I have. I was told by a former player that the hat was used in 1969. At the time I had no way of knowing. Later I learned a way of dating Wilson caps that put the manufacture in 1968. This gave added credence to the story that the hat was used in 1969.
I'm sure there are other hat manufacturers that can be dated also. Now if you were talking about modern day hats I have no clue.
Clint