To suffer the utmost deprivation to evil forces, usually due to a harsh legal judgment or gambling losses.
For the sake of charity: "He would give the shirt off his back to a man in need."
Legal losses (implicitly unjust): "We went to court, and I lost my shirt."
Gambling losses (implicitly unfair): "I went to Vegas and lost my shirt."
Matthew 5:39-42
But I say unto you, That ye resist not evil: but whosoever shall smite thee on thy right cheek, turn to him the other also. [40] And if any man will sue thee at the law, and take away thy coat, let him have thy cloke also. [41] And whosoever shall compel thee to go a mile, go with him twain. [42] Give to him that asketh thee, and from him that would borrow of thee turn not thou away.
Luke 6:29-30
And unto him that smiteth thee on the one cheek offer also the other; and him that taketh away thy cloke forbid not to take thy coat also. [30] Give to every man that asketh of thee; and of him that taketh away thy goods ask them not again.
Christ himself suffered this very loss:
John 19:23-24
Then the soldiers, when they had crucified Jesus, took his garments, and made four parts, to every soldier a part; and also his coat: now the coat was without seam, woven from the top throughout. [24] They said therefore among themselves, Let us not rend it, but cast lots for it, whose it shall be: that the scripture might be fulfilled, which saith, They parted my raiment among them, and for my vesture they did cast lots. These things therefore the soldiers did.[/b]