Asking him if he ever wears anything else besides his normal "proxy attire"
He likes what he usually wears and it's what he's comfortable in. If anyone asks if he wears anything else or why he doesn't, he'll question why it matters and explain that he's comfortable wearing what he does.
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50 Ways To Annoy Masky
Random50 Ways to annoy the fandomized-let me repeat, FANDOMIZED version of the glorious Tim. Short reasons, but keep them in mind if you ever plan on encountering him. Just to be safe...