To lose all or most of your money.
Потерять все или большую часть денег.
He’s stopped going to the races since he lost his shirt last year.
Он больше не ходит на скачки с тех пор, как он потерял много денег в прошлом году.
Mr. Matthews lost his shirt betting on the horses.
The man lost his shirt gambling and now he is in serious financial difficulty.
Мужчина потерял все на азартных играх и теперь у него серьезные финансовые неприятности.
Uncle Joe spent his life savings to buy a store, but it failed, and he lost his shirt.