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You can't get any of them from loot drops anymore. You could at one time on test, but they decided against it (it would ruin the purpose of making them special in the first place). The black bandanna was for those who were there when clothing was first introduced, the red bandanna was there during one of the events (can't remember which - possibly around the founders feast), and the black hat I believe was a glitch when you had the tri-horned hat and the black bandanna.
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