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I think your reasoning is sound, and think Does Not Like Shoes should be removed from this work's page due to misuse. You might wait for more responses, though.
Perhaps the Is this an example?
thread would be of interest to you.
This trope has been misused for years. Apparently there's a Wick Check that's a WIP and a thread in TRS might happen in the future
as in the Does Not Like Shoes page it states that it does not apply if the work portrays a society where no one wears them and well in the first Jungle Book that's the case since he lives in a Jungle among animals.
and in the second film the dress code of the village he lives in appears to be that none of the children are expected to wear footwear all of them are seen barefoot and only a couple of adult characters are seen wearing footwear.
so Mowgli's character not wearing shoes isn't just down to personal preference as its the societal norm of where he lives and if he was any other character he still wouldn't wear shoes because none of the children in the village do.
Edited by Plasticman1234