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Related to lose shirt: lost shirt
lose one's shirt
Fig. to lose a lot of money; to lose all of one's assets (as if one had even lost one's shirt). I almost lost my shirt on that deal. I have to invest more wisely. No, I can't loan you $200. I just lost my shirt at the racetrack.
lose your shirt
to lose all the money you put into something I lost my shirt because I didn't know anything about publishing at the time.
Usage notes: usually said about money that was invested
lose (one's) shirtSlang
To lose everything one has or owns.