A product, especially alcoholic liquor, but including recorded music, that is illicitly produced, distributed, or sold. The phrase "leg of a boot," goes back to the 1630s, using boot + leg to refer to that part of a boot. As an adjective in reference to illegal alcohol and is found from 1889 on and is American English slang. Presumably it was knives and pistols that were hidden in boots by smugglers and that led to the idea of hiding booze there, although this obviously cannot easily be done while the boots are being worn. An alternative understanding suggests that the word bootleg in reference to alcohol relates to the unpleasant taste of some illegal brews.
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