A Blessing On Your Head: Why Should a Jew Keep a Kippah on His Head?

For those who wear religious garb, it can be a spiritually rewarding experience. I wish I can say the same for me when I wear the kippah. Although it has certainly had its rewarding moments, on the whole, wearing a kippah has been something I have struggled with both in theory and practice. What I would like to do here is highlight both the reasons for wearing [or not wearing] the kippah while illustrating some of my personal struggles with this Jewish practice.

The kippah (כיפה, literally meaning "dome"), or what is alternatively called the yarmulke (יארמולקע; Yiddish word with its origins from the Aramaic "awe of the King," i.e., G-d) is a head covering that primarily observant Jewish males wear, although there are some non-Orthodox females that also wear a kippah. It is the most identifiable mark of a Jew, yet its origins are non-biblical in nature, which is where part of my frustration of wearing the kippah originates (The High Priest wore a head covering in Exodus 28:4, 7, 30, but this is a far cry from the obligation to wear a kippah). Why should that be frustrating? When you look at the history of Jewish practices, many of them were either created or evolved during the post-biblical era, which is fine. Religion is meant to evolve. Where I get frustrated is when we blur the line between custom and law, which at least for me, is what the kippah exemplifies. The kippah is first mentioned in the Talmud (more on that momentarily), and it was pretty much a practice for the particularly pious (חסידים). Only later did it turn into a widely accepted practice. Keep in mind that the Talmud does not forbid one to walk around bareheaded. Even during the Geonic period (6-11 c.), only those participating in services wore a head covering. The best way I can find to describe the legal status is the following: the Shulchan Aruch (Orach Chayim 91:3) and Mishneh Torah (Ahava, Hilchot Tefilah 5:5) require it in when praying in synagogue, studying Torah, and the like. Rabbis in pre-modern times had considerable debate as to whether there was an actual obligation (Orach Chayim 2:6 says there is an obligation), and that ambiguity leads me to believe that it is not a de jure obligation, although it is still a highly encouraged measure of piety. Still, many observant Jews treat it as if it were a de jure obligation. Even putting that debate to the side for a moment, what are some of the explanations for wearing the kippah?

1. Fear and awe of G-d. The Talmud does not make many references to obligatorily wearing a head covering, but one general reference to wearing a kippah is in Tractate Shabbat 156b. The parable in the tractate goes as such: The mother of Rav Nachman bar Yitzchak was told by astrologers that her son would become a thief unless the son changed his ways. Upon hearing this, the mother told her son to cover his so he will feel the reverence of Heaven (יראת הי). When using this parable we should consider a couple of points. First, should we base a practice on astrology? While astrology was considered to be science back then, we now know that it is hokum. Second, it is possible that it is an extreme case rather than a norm. Jews already had tzitzit and tefillin, amongst other signs to remind them of G-d's presence. Do we need more? Perhaps human spirituality is fragile enough where more mitzvahs to remind us of His presence is not a bad idea. 
2. Piety.  According to the Talmud (Kiddushin 31a), R. Huna did not walk four amot (אמות; cubit. Four cubits was the Talmudic definition of one's personal space) without having his head covered because he was humbled enough to be constantly reminded that there is always something above us. This talmudic passage could be why rabbinic authorities, including Chida, Magen Avraham, and Vilna Gaon (also see here) viewed the kippah as a measure of piety instead of a halachic obligation. If the kippah inculcated piety, I would be more appreciative of how such an external action could translate to internal awareness. It's hard to consistently have that level of piety. What happens when the desired effect is no longer there, or was never there in the first place? Has it lost its meaning of piety when Jewish individuals who commit reprehensible acts wear the kippah as a façade? I do wonder time from time how much the kippah has lost its meaning, at least in a sociological sense, when bad men commit wrongdoings while wearing the kippah.
3. Jewish pride. Even in the Middle Ages, Jews were more and more insistent on wearing the kippah to distinguish themselves from their bareheaded, non-Jewish neighbors because they were fed up with their Christian oppressors. Since Christians would take their hats off in reverence, Jews did the exact opposite (Taz 8,3). (This could explain why Sephardic Jews have not developed the same level of universal practice with the kippah.) Thankfully, we don't live in that world anymore. In an American context, Jews have great religious freedom, freedom that is unprecedented in the history of the Jewish diaspora. Rather than wear the kippah as a response to oppression, Jews in America, at least, can proudly wear the kippah as an expression not only of one's religiosity and Jewish identity, but as a sign of how far American society has developed in terms of religious tolerance. 
4. Jewish identity. 
• This one I would like to point out based on a recent study session with a chevruta of mine when we were studying Kitzur Shulchan Aruch. Jewish law dictates that Jews are supposed to keep certain particularistic practices to distinguish the Jew from the non-Jew/gentile (Leviticus 18:3) in order to prevent assimilation (Deuteronomy 12:30). The Kitzur Shulchan Aruch discusses this in the specific context of wearing clothing. Here's an important question: which non-Jews are we not supposed to emulate? We don't live in the same world that our ancestors did. Jews don't live in ghettos or shtetls. The world is much more globalized than it used to be, and there is a lot of heterogeneity when it comes to what non-Jews wear. Given the wide variety of clothing in modern times, it's all the more difficult to say that wearing a certain style of clothing is a prima facie form of assimilation. We don't live in a world in which Jews wear distinctively Jewish clothing. Since many observant Jews buy their clothes from non-Jewish distributors, Jews have less ways to distinguish themselves in terms of clothing. Aside from wearing tzitzit, something which a sizable amount of observant male Jews tuck in anyways, the only way the Jew has to externally identify himself as Jewish, at least in terms of apparel, is the kippah. As such, the kippah has more relevance in terms of symbolism than it did in the past.   
• Wearing a kippah in everyday situations not only shows that you are a Jew who observes Jewish laws and practices. There are enough identity politics in the type of kippah that one wears that one can determine the political or religious affiliation simply by looking at the type of kippah. For instance, the black velvet kippah is worn by yeshivish types. A crocheted kippah is typically worn by Modern Orthodox or religious Zionists, although there are some non-Orthodox Jews that wear them. The satin ones are worn by non-Orthodox Jews who borrow it from the synagogue on a one-time basis because they don't normally wear their own. A lot can be said about the type of Judaism one practices based on what wears on one's head. 

Postscript: Should the kippah be something worn by all Jewish males or return to being a status symbol of true piety? This question gets at the true struggle I feel with the kippah because I think that the kippah should not simply symbolize one's Jewishness, but one's level of internal piety. The vast majority of us do not feel a 24-7 closeness to G-d (דבקות). Because I do not consistently have that sense of piety or humility, there are times that I feel out of place or dishonest wearing the kippah. There is that part of me that feels that the kippah is for the truly pious. Conversely, it very well could be precisely because the דבקות is not always there is when I need the kippah as a reminder that G-d is above me. I will continue to have that internal conflict as to whether the kippah is meant to be a status symbol of one's inner piety or if it is meant to engender a further sense of inner piety. Whichever approach I take, I'm just glad that I can continue having this struggle over something that isn't unambiguously accepted under Jewish law.