"to lose your shirt"
to lose all of your money
to lose the majority of your money or investments
be cleaned out, be in arrears, be ruined, be taken to the cleaners, become insolvent, break, close, crash, default, dishonor, drop, end, finish, fold, go bankrupt, go belly up, go broke, go bust, go into Chapter 11, go out of business, go to the wall, go under, go up, lose big
This man has literally lost his shirt
. - - - - ->