Green’s Dictionary of Slang

blowed-in-the-glass (stiff) n.

(US tramp) an elite tramp.

1895		Harper’s XCI 778/2: You wants me to be a blowed-in-the-glass stiff.
1903		St Louis Republican (MO) 30 Aug. 52/1: You’re a blowed-in-the-glass hobo now.
1907		J. London Road 114: He was a true ‘profesh,’ a ‘blowed-in-the-glass’ stiff, and as such received all kinds of latitude from the hall-men in authority.
1916		‘A-No. 1’ Snare of the Road 12: One of the profesh? A reglar blown-in-the-glass stiff?
1921		P. & T. Casey Gay-cat 13: The years I’ve spent a-trainin’ of him to be a blowed-in-the-glass stiff [Ibid.] 107: One o’ them bums used ter be a blowed-in-the-bottle as good as yuh ’n’ me. [Ibid.] 108: When I seen him last he was travelin’ hobo fashion as a real blowed-in-the-glass.
1925		J. Tully Beggars of Life 156: You look like a blowed-in-the-glass stiff.
1931		Irwin Amer. Tramp and Und. Sl. 31: A ‘blowed in the glass stiff,’ [...] is one who never works, one in the know, and able to take care of himself in any situation.
1947		C.B. Davis Jeremy Bell 53: ‘What’s a blowed-in-the-glass stiff?’ Jeremy asked. Henry took a drink of beer and grinned. ‘That's a regular professional hobo tramp that just travels around the country and won't work at all unless he's made to and begs at back doors’.
1962		H. Swados Years of Conscience 339: He was a true ‘profesh,’ a ‘blowed-in-the-glass’ stiff .