Analysis of information sources in references of the Wikipedia article "Boot" in English language version.
It's been widely suggested that the "bootstrap" metaphor originated in the legendary tales of Baron von Münchhausen. As Chris Waigl recently pointed out on the Eggcorn Database (commenting on "boots-trap"), the original German version has a scene in which Münchhausen gets out of a swamp by pulling on his own hair. In an American retelling (supposedly), the Baron uses his bootstraps to pull himself out of a similar predicament. None of the 19th-century cites I've seen allude to the Münchhausen story -- instead, they often refer to pulling oneself over a fence or up a steeple. So if Münchhausen really pulls himself up by his bootstraps in an American version (which I have yet to verify), then the writer probably took advantage of preexisting imagery for an absurdly impossible task.