This is a grey hat that he wears earlier in the story. You can get most of his clothes from earlier in the story but I haven't found out how to get this hat.
John's Hat
How to get this hat
red-dead-redemption-2
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Best Answer
To get John's gamblers hat you need to during the epilogue part 1 have it knocked of and be picked up again. YOU CANNOT REPLAY MISSIONS TO GET IT. So sorry if you have already completed the epilogue.