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Tolkien's statement [from a letter but noted in the Annotated Hobbit] is curious here, as there is seemingly no [surviving?] reference to this booting in the drafts, now that we have The History of The Hobbit in print... but as you note, in any case Bilbo is booted in illustrations made by JRRT himself.
As for The Lord of the Rings, can we find some later reference[s) to Hobbit feet that would suggest no bootings for Frodo, Sam, Merry, Pippin?
I can't recall any at the moment, but it's a relatively long tale. It is noted [I think] that some Stoors wore boots in muddy weather, so in general it's not like no Hobbits ever wore boots.
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