Is it forbidden or just disrespectful to wear a kippah with ads on it while in shul or learning?

Question

When my kids were in yeshiva, the school had a policy that they were not allowed to wear kippot that had any writing other than their name, or "Yerushalayim" or something similar. I.e. - no logos like from sports teams or store ads (Yes, they exist. It looks a bit meshugah, but I think it's a clever idea.) The principal considered this "advertising to G-d", in a sense, and this was a Chilul Hashem while in the yeshiva. (I think he didn't want them to wear such kippot even outside of the yeshiva, but he couldn't enforce that.)

Are there any halachic problems with wearing an "advertising" kippah (as described, above)? Is it a chilul Hashem or just considered inappropriate or disrespectful to wear such a kippah in shul or while learning in a yeshiva, Bet Midrash, or for that matter even learning in private at home?

Answer 1

Shulchan Aruch O.C. 90:23

הבגדים המצויירים אף על פי שאינם בולטות אין נכון להתפלל כנגדם

It is not proper to pray facing colorful garments, even if they do not protrude.

Beis Yosef, citing Rambam, explains that the reason it is preferable to pray close to the wall is in order to not see distracting things.

If these kippot have drawings or writing on them which catch one's eye and are distracting (as I would assume an advertisement would be designed to be), then the one wearing it is bringing a distracting image into the shul and putting it in front of everyone standing near him.

Answer 2

1 Aish says

The Talmud says that the purpose of wearing a kippah is to remind us of God, who is the Higher Authority "above us" (Kiddushin 31a).

2 Halachipedia quotes the Gemoro (Shabbat 156b) to say

“A Kippah or Yarmulke is a religious head covering worn to inspire fear of heaven in the mind of the one wearing it as it reminds the wearer that G-d is above a person all the time.”

3 Wikipedia quotes amongst other things

Covering one's head, such as by wearing a kippah, is described as "honoring God" (Shaar HaTzion, OC 2:6. )

4 Daily Halacha.com says:

There is considerable debate among the Halachic authorities as to whether or not wearing a Kippa constitutes an outright obligation or is just "Midat Hasidut" (measure of piety).

Whether there are halachic issues will depend on your position on this debate.

But, the question will always remain as to whether the purposes in 1,2 and 3 are achieved by the use of logos like from sports teams or store ads.

If the custom of using these logos becomes widespread, then it may still be possible to remain reminded of the Higher Authority "above us" to have “ fear of heaven” and to be “"honoring God". But 'early adopters' of this practice may find it more difficult to focus on the purpose of the kippah because of the interest their kippot will excite.