lose one's shirt

present singular third person loses one's shirt · participle present losing one's shirt · participle past lost one's shirt · past lost one's shirt

1. idiomaticTo lose all of one's money; to go broke; to undergo financial ruin or disaster.

   Since nearly losing his shirt in a business deal a few years back, he investigates new opportunities more cautiously.

   1 more example

   Generosity indeed, but how difficult will it be for some penitent punters to drop a coin in the "sin box" if they happen to have already lost their shirt on a bet placed with Paddy Power?

   2010 April 27, “Church bets on power of sponsorship”, in The Guardian