Our Sages said: Just as the Holy One clothes the naked, as it is written, And Hashem God made for Adam and his wife garments of skin, and He clothed them (Bereishis 3:21), so you, too, clothe those who are naked. In truth, it is a great obligation to have mercy on the poor with regard to giving them clothing even more than with regard to feeding them. For when it comes to food, the poor person can suffice on less — he can toil all day, earn a little and buy some bread in the evening. Not so when it comes to clothing, for which he needs a larger some all at once, which he cannot afford. Because of this, he carries on while his garments become tatters, and all he has left is one ragged garment. His life is no life. Therefore, it is befitting that the merciful Jewish people, descendants of merciful ancestors, have mercy on the poor.
And if an individual has been blessed by Hashem with wealth and honor, this is what he should do: Every festival he should have new clothing made for himself and for his family (from head to toe!), and he should give away his used clothing to deserving poor people. In this manner he can be proud of his wealth. And although the Sages taught that one should designate the best of what one has for charity — but they also said that “your life comes first,” so he comes first to wear the new garment. He will exchange the old for the new.
