The logos look more like 1970s era to me. I should preface this by stating I am not familiar with these Hats, and perhaps someone on this board is. But I have collected these types of souvenirs for 20+ years, and I am very familiar with similar items sold at the Ballparks (and the evolution of team logo variations).
It would be easy to pass these off as 1940s or 50s. Neither the Cubs or Yankees logos have changed much over the past 6 decades. But there are subtleties that indicate the age of the items in question. The Yankees Top Hat & Bat logo on your Hat looks a bit more simplistic than earlier examples. This was a sweeping trend of the '70s. Just look at how the Pennants and Pinbacks of that era became more basic and less artistic.
Same for the Cubs logo. That thicker "C" really looks more '70s to me. This is just my educated guess after having viewed hundreds of items like this. I think that the seller embellished the age of these Hats by about 3 decades or so. The condition would indicate the same. There is also a chance that the plastic "Player" charms were added at a later date (to make the Hats appear older). The Player figures do look more '50s - '60s than the logos on the Hat Bands.
Sorry to ramble, but I believe late '60s/early 70s for both of these Hats. Still cool items, and still very collectible. Perhaps just not as old as the original seller indicated. Hope this helps, and I'm eager to hear what others think!
Mark
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