You're seriously overthinking it: The appearance of clothing is officially just that -- an appearance; it's really part of the body. Medicham's belly dancing outfit is officially just thick thighs; Delphox's robe is all fur.
So the clothing is actually melded onto the Pokemon itself, that's kind of creepy when you think about it.
But even the things that look like clothes like Machoke's power belt and posing briefs and Hitmonchan's sleeveless shirt and skirt-thing are part of the Pokemon's body. I can buy Delphox having a robe-like covering of fur, I can buy Medicham's belly-dance outfit as being part of her body but if it's colored differently and looks like it's made of a different material, then it has to be clothing. Which makes me wonder- were they born with the clothing on? Does Machop just grow a pair of briefs and a power belt when he evolves?
Also, we have waited seven generations and Nintendo STILL has not created a werewolf Pokemon? Why? Bandai created Weregarurumon for Digimon and he looked awesome.Lucario is a jackal and that doesn't count.
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