Whitman O'Neil,
It has always been my understanding that tatterdemalion was a lively, rattling, machine-gun word, one chosen by many writers as suitable accompaniment to invective or disparagement. Here’s Lady Wishfort, in William Congreve’s play The Way of the World: “Frippery? Superannuated frippery? I’ll frippery the villain; I’ll reduce him to frippery and rags, a tatterdemalion!”. Or James Joyce, in full flow in Ulysses: “Florry Talbot, a blond feeble goosefat whore in a tatterdemalion gown of mildewed strawberry, lolls spreadeagle in the sofa corner, her limp forearm pendent over the bolster, listening”.
But where it comes from is open to argument. The first part seems pretty certain to be our English tatter. Some writers trace the second bit to the French maillon, swaddling clothes. Others say it comes from the Italian maglia for undershirt or (British English) vest. Support for this comes from the very earliest use, by Ben Jonson in 1611, which he spelt as tatter-de-mallian, reportedly said as though it were Italian.
But to double check I went to my favorite etymology site and they gave me this:
According to the Online Etymology Dictionary
In reply to:
tatterdemalion
"ragged child, person dressed in old clothes," 1608, probably from tatter, with fantastic second element, but perhaps also suggested by Tartar, with a contemporary sense of "vagabond, gypsy."
But when I pulled out my 1913 Webster's Dictionary I got this:
In reply to:
Definition: \Tat`ter*de*mal"ion\, n. [Tatter + OF.
desmaillier to break the meshes of, to tear: cf. OF. maillon
long clothes, swadding clothes, F. maillot. See {Tatter}, and
{Mail} armor.]
A ragged fellow; a ragamuffin. --L'Estrange.
So I guess the truth of it is that no one knows.
Rev. Alimae