Why do many Jewish men wear head coverings (variously referred to as “yarmulkas,” “skullcaps,” and “kipot”)?
The customary Jewish head covering (for simplicity, we’ll call it a kipa (singular of kipot), although all the terms refer to approximately the same thing) is a sign of humility for men, acknowledging what’s “above” us (G-d). An additional explanation is that in ancient Rome, servants were required to cover their heads while free men did not; thus, Jews covered their heads to show that they were servants of G-d. It’s necessary for men to cover their heads during certain prayers (whether it be by a kipa or another headcovering), and for one making blessings all day, it’s inconvenient to keep donning and removing a kipa. In some places, the type of kipa and way of wearing it expresses affiliation with a particular yeshiva or political viewpoint. In other places, it doesn’t really matter. Many Ashkenazi rabbis acknowledge that wearing a head covering at all times was once considered an optional “midat chasidut” [pious act] but that nowadays, full-time head covering is the norm except unde