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dudes should feel ok with wearing (good) hair pieces. women do it all the time, no shame in it guys. if you can't or don't want to rock bald i will totally support you having an array of great wigs.
yeah pokemon can probably go bald, since they can catch diseases, and their hair canonically grows instead of just being a static immutable thing. though we've not seen much about genetic abnormalities in pokemon, except shiny pokemon, if that's the equivalent of albinism. imagine a conjoined pokemon.
