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First up, an apology: I messed up with 'plant-based'; I forgot that clothes in LotR are more likely to be wool than cotton. Either animal-based or metal would have been a better choice to rule out.
Okay. Where do you wear things? Your head (ruled out), your hands, your feet, your legs, your torso, or as an accessory.
Hands: either a ring or a glove. Almost all rings are ruled out because we know exactly who made them, or because they're around in the First Age. I can't think of anyone wearing gloves.
Feet: does anyone have noteworthy shoes or boots? It can't be a dwarf, because they presumably wouldn't fit Eowyn. Tom wears big boots to confront a troll, and Tom Bombadil has yellow boots that Eowyn could probably get her feet into.
Legs: I... don't think there's any significant trousers? Tolkien doesn't really go much in for clothing descriptions outside the Hobbits, and we know it's not theirs. (Though, hmm... 'Hobbit thing' is ambiguous; does that imply that it was owned but not made by a Hobbit?)
Torso: armour is a possible, and is going to be a nightmare - about the only one we can rule out is the Mithril vest! If not armour, we're looking at some sort of leather jerkin or wool top (but not Bilbo's weskit). Perhaps a costume someone disguises themselves in, though the only one I can think of is Frodo's Orc-armour. (Is Gollum's loin-cloth from the book?
Accessory: a cloak springs to mind. I don't think we know what the Lorien cloaks are made of, and they could have been made by Feanor. Or we could be looking for an item of jewellery, like a brooch or necklace (without a prominent jewel). Bombadil pulls a brooch out of a barrow, Pippin drops one in Rohan, and the Rangers of the North wear a silver star. Necklace... there's the Necklace of Girion, which has jewels in it but isn't one. And I suppose there's the chain the Ring hung on. (Would Pearl Took's pearl necklace count as a jewel?)
Or how about backpacks? Most of the Fellowship have them, and they could be either wool or something like canvas. Something like 'Sam's pack' might be unique enough to be a 20 Questions answer (though that one would be a Hobbit Thing).
And belts, as well... Boromir's is the only one that jumps to mind, though others are mentioned (Balin has one when he comes to visit Bilbo).
There... really doesn't seem to be an easy way to narrow this down.
hS
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