There are just plain dumb decisions that are made in life. At times when we make these stupid decisions, God in His mercy will deliver us from the consequences. If this happens, do not think God approves your actions - He is just showing amazing mercy to you in the midst of them. But there are some decisions God decides to allow us to face - with the full measure of the consequences being given to us. This proverb tells us about two of them.
The first has to do with a man acting foolish financially. When someone becomes surety for a stranger, that is a very foolish thing to do. This proverb tells us to even take a man's garment when this happens. Just as a reminder, surety is when we co-sign a loan - or guarantee another person's debt. If they default on the loan - we are on the hook for what they owe. The reason this is so foolish here is because someone is doing this for a stranger. He doesn't know the man - and is not related to him. He is just guaranteeing a loan for someone he does not know. He does not have a clue as to his character or his integrity - he just lays down his money to guarantee this man's borrowing. Surety is discouraged for anyone - but this should be a no-brainer when it comes to a stranger. With a family member of friend, we at least have a sense of their character and whether they will be likely to repay the loan. But a stranger - we know nothing about him. Thus, Solomon tells us to take this man's clothes when the loan defaults. This is something that hopefully will teach him a lesson about guaranteeing the loans of others - especially those he does not even know.
The second scenario is when a man hires a prostitute for sex - and offers her a pledge as payment. Adultery is a very foolish sin - but to offer someone our name as pledge is really foolish to another level. Amazing as it may seem, this is what Judah did when he hired his daughter-in-law Tamar as a prostitute. Tamar was not being a harlot. She was simply desiring that Judah's family line fulfill their duty in raising up sons for the deceased. When Judah did not have the money in hand to pay her - she asked for his seal and his cords. These were things by which a man could be known if they were seen. This was not wise for him - but it gave her the proof she needed when her adulterous father-in-law wanted to have her stoned for playing the harlot. When Judah saw his own seal and cords, he was humiliated and withdrew his call for her death.
No one wants to be humiliated by their sin. But there are times when it is a far better thing to be humiliated and learn than to escape humiliation and continue in sin. God is amazing how He delivers us from sin and from the world around us. May God give us grace to embrace that deliverance - and truly be wise.