Take his garment that is surety for a stranger: and take a pledge of him for a strange woman.
Taking risks does not prove courage or wisdom; it is usually evidence of haste and folly. Unnecessary risks tempt God, and He will judge such presumption. This proverb teaches that men should also judge those who take foolish risks. Because they show the character fault of foolish risk taking, security should be required in any transactions with them.
Solomon often warned against suretiship (Pr 6:1-5; 11:15; 17:18; 22:26-27; 27:13). See the comments on 6:1. In fact, our proverb has a twin in 27:13. A great part of wisdom is avoiding risks that could cost you financially or in other ways. Wise men strive to preserve capital, not foolishly risk it to loss by naïve and ignorant optimism. Prudent men avoid danger and risk; simple men pass on foolishly and get punished (Pr 22:3; 27:12).
Being a surety is guaranteeing the performance of others, as in co-signing loans. Doing this for a stranger, due to haste or pride, can create serious financial trouble. If the stranger does not perform, creditors can enforce the contract on the guarantor - the fool who co-signed the deal. It was a big temptation to kings' sons to guarantee others. But if a person has exposed himself to such risks, how can you trust him to make good to you?
Solomon gave his son a rule about business partnerships. Do not enter transactions with risk-takers, unless you take security of them. Since garments were valuable possessions in Bible times, he suggested taking the garment of risk takers as a performance bond, security deposit, or earnest money (Gen 38:13-18; Ex 22:26-27; Deut 24:10-13). By taking a security deposit, a wise man can safely enter contracts with foolish men.
The second clause of the proverb has an ellipsis, words intentionally omitted to shorten the sentence and increase the force. Pledges, or security deposits, should also be required from men who have dealings with strange women. For the immoral, or amoral, lifestyle of a whoremonger indicates that you should not trust him in business or financial transactions. To protect yourself, you need to take a security deposit again.
It is wonderful to meet godly men, with whom you can enter partnerships and transactions and not worry at all. But men who are not disciplined financially or morally are not good business partners. They should be avoided. A wise man will not risk his own financial life by trusting a person who takes unnecessary risks with capital or women.
Reader, it is better to be safe than sorry. Resist all the appeals of others, and the pride and greed raging within, to be a risk-taker. And avoid commitments with whoremongers.