"To show that a character is in such dire financial straits that he's literally "lost his shirt", the otherwise naked character will resort to wearing a large barrel◊ held up with suspenders. Primarily seen in cartoons. This image probably came from a punishment for public drunkenness in Germany and England, where drunks had to wear a booze barrel (a "drunkard's cloak" or a "new-fashioned cloak"). It's unclear how barrel wearing became associated with bankruptcy (perhaps from the assumption that public drunkards are always hard up for money?), but the trope stuck."