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Golarion isn't earth and might have developed jeans/baseball caps at some point over its massive history that might conflict with the order of how they were invented in our world.
Well, that's a good point. Still feels odd to me to see a baseball cap in a fantasy RPG, but it seems like these days people care less and less about that kind of thing.
Also that might be a different lumberjack in the festival than Dingo Dray, the rest of his named pictures have a pretty consistent look that's different from the chapter opening picture.
Hmmm... I guess that's possible. The lumberjack in the other two pictures also has a beard, a red flannel shirt and suspenders, but a different hat. Dingo's hair is redder than the guy in the chapter opening illustration. I still think it's supposed to be him though. :-)