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In the Pokémon XY series Ash was dressed up and looking a bit like Calem, the male player character from XY games.

In the sun moon series he is dressed up and looks like sun from the Pokémon sun moon games.

I am not sure about the other regions but I know in kanto and orange islands he doesn't...

Why is he dressed up like that?

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The anime is used to promote the games and merchandising opportunities. This is just another step towards that goal.

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