Losing Your Shirt

Losing Your Shirt

Informal; a situation in which one makes such a bad investment decision that he/she loses everything he/she owns. For example, if a business venture goes bankrupt, an investor may be said to lose their shirt if they also must sell their house to repay the business' debt. Losing your shirt has a strongly negative connotation because it implies that one must sell one's shirt to pay liabilities. See also: Rio trade.