read for free http://www.emunas.com/audio/Shalosh_Seudah_Torah/39_emor.pdf and from Gutman Locks“Why Should I Wear a Kippa?”Mikey, whose real name is Mordechai, came up to me at the Kotel wearing tzitzis (fringes) but no kippa! (head cover) This is highly unusual. Tzitzis is a much more “advanced” mitzvah than the kippa. Although tzitzis is commanded directly from the Torah, and kippas are “merely” a rabbinical custom, wearing a head covering is common to many more Jewish men than wearing tzitzis.When a Jew becomes a baal t’shuvah (returnee) he begins to follow the commandments. There is a lot of leeway in the beginning as everyone understands that you are just starting. Each of us begins at our pace and goes as far as we want. If it is pleasing, inspiring, we go on and on until it is hard to distinguish between a baal t’shuvah and a Jew who has been raised in a Torah-observant home.
So, when I asked Mikey what he was doing walking around wearing tzitzis, and even wearing the garment outside of his shirt where everyone could see them, but not wearing a kippa, he challenged me asking, “Why should I wear a kippa?” I knew what he was going to say.
“Tzitzis are a Torah commandment. G-d told us to wear them! Kippas are just a rabbinical custom. Why should I wear a kippa? Why did they make up that rule?” He asked.
“The rabbis did not just invent the custom.” I answered. “Kippas are based in the Torah. Nowadays we do not have a Temple, so there are no kohaneim (Jewish priests) serving in the Temple. This means that our individual spiritual service is even more important than it was back then. The kohaneim always wore a head covering when they served, so the rabbis instituted the custom that we too should wear a head cover.”
I went on, “There is a deeper reason to cover our heads. When you wear a covering on your head there is always something above you.” I looked up as if I was trying to see my hat, and then even above that. “When you wear something on your head it reminds you that there is always Something above you.”
He got the idea. He smiled, and walked away with a kippa on his head. I saw him the next day wearing a new colorful kippa. I commented on how nice it was. With a big smile he said, “Well, you explained it to me.”