Biloxi Daily Herald, November 19, 1919. A vital sartorial tip: Never attempt to wear a barrel without suspenders. Unless you’re a showgirl working a gimmick to get a little press, at least. (Hey, does anybody know what a “picture hat” is?)
So here’s what I can tell you about the origins of the wearing-the-barrel trope qua signifier of destitution. Near as I can tell, it was born from the confluence of two prior memes. On the one hand, you’ve got the precedent of the “Drunkard’s Cloak,” 
which was a medieval and early-modern legal incentive against public inebriation. The association between habitual intoxication and poverty seems pretty clear, right?
The second precedent is the ascetic Greek philosopher Diogenes (circa 412-323 B.C.),
who supposedly made his home in a big clay jar. “Jar” somehow got mistranslated as “barrel” in popular consciousness from the early-modern through the Victorian era. (And yes, there did used to be popular consciousness of Diogenes.) I’m guessing the guy-in-a-barrel has real early theatrical roots and takes off from there.
Chicago Inter-Ocean, August 11, 1874. It was strongly talked of, see? It was not the passing subject of gay badinage and persiflage, nor something obliquely alluded to in a manner that went over the heads of most. The talk of lynching was strong. 
Omaha Morning World-Herald, May 13, 1895. Even as tied-to-the-tracks dramas go, this story’s a weird one. Or even as real-life precursors to 
I forgot to cross-promote my most recent film review for the Chicago Reader, of Niko Von Glasow’s excellent documentary 
Columbus Enquirer, July 9, 1909. I sympathize with this young woman, but at the same time I find the sheer mythological purity of her plight insanely pleasing. 
Savannah Tribune, November 9, 1922. Call me judgmental, but that is just plain bad parenting. 
Chicago Inter-Ocean, September 2, 1894. That bit from silent movies in which the bad guy ties his victim to the railway tracks before an oncoming train? That is totally Stuff People Actually Used To Do. Not just once or twice either. It seems to have been an enduring favorite in the Blackguard’s Playbook. 
Philadelphia Inquirer, February 3, 1885. Ciboire de tabernac, il aime pas trop les gosses, ce dingue la. 
Los Angeles Times, April 3, 1887. This here item is a Rosetta Stone in relation to 