The word drag in the context of describing the act of wearing clothes of the opposite sex first emerged in various newspapers in the early 1870s. There are several theories as to wear this comes from - including Yiddish trogn, meaning "to wear", and Romani indraka, meaning "dress" - but the most accepted explanation is that it simply comes from the verb to drag, on the notion of clothes dragging on the floor. In Middle English and Old English, that was draggen and dragan, respectively, and dragan comes from Proto-Germanic dragana and Proto-Indo-European dreg, which had the same meanings as today. The term drag racing first appeared in 1947, probably tracing to an old slang word meaning "buggy" (and this also derives from the verb, because horses would drag buggies).
Hello! I'm Adam Aleksic, a sophomore studying government and linguistics at Harvard University, where I co-founded the Harvard Undergraduate Linguistics Society. In addition to etymology, I also really enjoy politics, vexillology, geography, board games, conlanging, and law.