In The Hobbit Gollum thinks about what he has in his pockets-- but that doesn't mean he's wearing trousers, just that he owns some. He might have his old shirt, shoes and trousers (with the string, etc. from his old life still in the pockets) folded up safe on his island somewhere, to be worn on a suitable occasion-- which never comes. That's terribly sad. You know, I think we may owe the entire Lord of the Rings to Tolkien feeling sorrier for Gollum than he ever expected to while he was writing Riddles in the Dark.
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