“Lose one’s shirt” (become impoverished)

To “lose one’s shirt” is to lose everything. “Lose your shirt” was cited in print in 1886, in a story about gambling at draw poker. “Uncle Sam (...) has not ‘lost his shirt’ in the transaction” was cited in 1897.
 
“The man who rolls up his sleeves seldom loses his shirt” is a saying that dates from at least the 1940s.
     
 
Wiktionary: lose one’s shirt
Verb
lose one’s shirt
1. (idiomatic) To lose all of one’s money; to go broke; to undergo financial ruin or disaster.
 
(Oxford English Dictionary)
to lose one’s shirt: to lose all one’s possessions.
1935   E. B. Mann Thirsty Range xi. 144   He hit the market..about the time the bottom dropped out of it. He lost his shirt!
         
1 August 1886, Galveston (TX) Daily News, “Draw Poker” (Cincinnati Enquirer), pg. 7, col. 5:
“Step out when you are a good winner, whether the others like it or not, as you are not living for them, or not even playing for their comfort, but to beat them for all there is in them; and if you are losing don’t stay all night and lose your shirt in the sad attempt to catch on, for nine chances out of ten you won’t.”
 
2 July 1889, The Daily Independent (Monroe, WI), Correspondence, pg. 1, col. 3:
One of our men went to Browntown the other day, and got into a racket with a sucker, and lost his shirt.
 
2 November 1897, Duluth (MN) News Tribune, “The Union Pacific Sale,” pg. 4, col. 3:
UNCLE SAM has finally gotten the Union Pacific railroad off his hands, and (as is not always the case) he has not “lost his shirt” in the transaction.
 
17 August 1919, Philadelphia (PA) Inquirer, “Some Tom Mix Sayings,” pg. 23, col. 2:
“I am not good in a big city. If I sat in a big corporation meeting in a room hung with beautiful curtains with mahogany tables and chairs, I would lose my shirt; but if those millionaires would come out to my ranch, where I would be surrounded by my cattle and my horses, I could drive a harder bargain than was ever driven by Rockefeller or Carnegie.”
   
Google Books
August 1922, Cosmopolitan, “My Week in Cuba” by Ring W. Lardner, pg. 51, col. 1:
But how a person can keep beating thirty-five to one shots at a roulette table and then go out the next day and lose your shirt on a three to five shot at the track is a misery to me.
 
Google Books
Dock Walloper;
The Story of “Big Dick” Butler
By Richard Joseph Butler and Joseph Driscoll
New York, NY: G.P. Putnam’s Sons
1933
Pg. 270:
It’s bad enough to lose your shirt in the radio business and everything else you try your hand at, but to lose your home is worse still.
 
Google Books
Unpopular Opinions;
Twenty-One Essays
By Dorothy L. Sayers
New York, NY: Harcourt, Brace
1946
Pg. ?:
The man who rolls up his sleeves seldom loses his shirt.