To lose everything. This term alludes to betting on or investing everything one owns in some venture, but at one time it meant to become very angry (in effect the opposite of keep your shirt on). The current cliché, aided and abetted by the Great Depression, is a twentieth-century locution. “He hit the market . . . about the time the bottom dropped out of it. He lost his shirt!” (E. B. Mann, Thirsty Range, 1935).