So after he made his comment about it being the head of the year and how it would be a good time for me to get a new hat, I responded a second later by saying, “I’ll tell you what. I’ll get a new hat, if you come with me when I visit the sick in the hospital.”
He looked at me like I was from another planet. “What does one have to do with the other?” he asked, and then he walked away.
If he didn’t know what I was referring to, it would have taken me too long to explain it to him, so I didn’t try.
In the years since, my life experiences have “explained” this issue to me. I’ve seen that over time I grew more comfortable with the idea of wearing a nice hat and I more often wear it to shul – and even on occasion wear it during the davening. I do it not because anyone told me to do it, rather I told myself it’s what I wanted to do.
Also, in the years since I’ve heard about bad things happening because people who are dressed like a very religious person are anything but religious in their actions. More than 99% of Orthodox people who are dressed in a distinctive religious fashion are good people. Unfortunately, there are some who are not and it’s important not to take for granted that just because someone dresses a certain way, they are a good person.
After all, you don’t want to invite well-dressed bank robbers to your Shabbos table.
Still and always, the most important quality that a person possesses is what’s inside.
Good middos trump distinctively religious clothing any day.
However, what I have also come to see is that if a person has good middos AND dresses in a way that lets the world know they are Jewish, that’s the most powerful combination of all.