Q. What sort of clothing should one wear on Rosh HaShanah?
The Shulchan Aruch says that one should always dress as if one were appearing before a monarch. If this is the case with a monarch of flesh and blood, all the more is it so in the presence of the King of Kings. But even that may not be enough.
Rabbi Bunem of Pshyshke said, “Once a person wearing fine clothes came to ask for charity. Because he looked wealthy he had a hard time explaining why he needed help. Yet another person who came dressed in rags was given help at once.
“So it is with us. A self-satisfied person who asks God for help needs to explain himself and plead for Divine support. But one who comes with a broken heart is answered at once.”
We should all dress as neatly as possible and certainly not in rags. But the issue is not our physical clothing but our spiritual situation.
If we show off to God we will not achieve an answer nearly as quickly as if we humble ourselves and really mean every word of our entreaties.