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It's hard to say...
There's overlap between the Ashs barring Unova Ash.
If anyone payed close attention, Ash cooling down in Johto led to his more leadership-esque personality in Hoenn. Hoenn to Battle Frontier caused Ash to gain a bit more insight on battling, causing him to have better strategies in Sinnoh, as evident in the Lily of the Valley Conference.
... And Unova Ash just threw it out the window.
Funny, because a Japanese friend of mine, tries to resolve this with "he's.. just holding back", but I don't buy it.
As for clothing, I find AG Ash to be very form fitting for him, as a character.
DP is a close second, but I personally don't think Ash can rock the black vest without a much more mature demeanor than what he exemplified in Sinnoh.
Unova and Kan/Joh are bottom tier for me, although Unova wins out simply because Ash looked like a retard in his original clothing.
I wasn't really a fan of the 'hat turning' thing either. When AG/DP Ash did it, it had much more meaning to it, due to how seldom of an occurrence it was, and it usually was saving a loved one like May in Movie 9, or Pikachu in late Hoenn. He also did it in important battles such as the one with Tobias in Sinnoh.
