Green’s Dictionary of Slang

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

also blowed-in-the-bottle, blown-in-the-glass stiff
[blown-in-the-glass adj. + stiff n.1 (5a)]

(US tramp) an elite tramp.

Harper’s XCI 778/2: You wants me to be a blowed-in-the-glass stiff.
[US]St Louis Republican (MO) 30 Aug. 52/1: You’re a blowed-in-the-glass hobo now.
[US]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.
[US]‘A-No. 1’ Snare of the Road 12: One of the profesh? A reglar blown-in-the-glass stiff?
[US]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.
[US]J. Tully Beggars of Life 156: You look like a blowed-in-the-glass stiff.
[US]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.
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’.
H. Swados Years of Conscience 339: He was a true ‘profesh,’ a ‘blowed-in-the-glass’ stiff .