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I happen to have an unusually large head to begin with, so that only the largest knitted kippot that I spend time stretching out even more barely fit. But now that I'm growing out my hair to donate for children with cancer, I have yet to find a kippah that fits. And since my hair is long, the smaller kippot that are secured with bobby pins tend to flop around all over the place.

Are there any other type of Kippot one could wear that work well with long hair? Perhaps a turban? I've been wearing a specialty extra large hat but it's my only one and doesn't look particularly religious.

Aaron
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    Are you just asking for advice about what sort of large hat "looks particularly religious"? Seems primarily opinion based. – mevaqesh Aug 16 '17 at 19:15
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    related: https://judaism.stackexchange.com/questions/75300/is-there-a-prohibition-against-long-hair-for-an-orthodox-jewish-man – Loewian Aug 16 '17 at 19:17
  • also: https://judaism.stackexchange.com/questions/37784/does-a-man-with-long-hair-need-to-become-a-nazir – Loewian Aug 16 '17 at 19:23
  • When I had long hair, I wore a regular kippah serugah without significant difficulty. Some chareidi styles might fit better, as they're supposed to stay on without any clips. – Noach MiFrankfurt Aug 16 '17 at 21:30
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    I'm thinking that you could try a Bucharian kippa. They are quite huge and tend to stay on your head without bobby pins or clips. Of course, there is no requirement to specifically wear a kippah. You could go "all out" and wear a Borsalino! – DanF Aug 17 '17 at 17:15
  • @DanF The Borsalino is basically what I wear now. It took me over a year of hat shopping to find one that fit with my hair. In general the Bukhari ones are not big enough to fit my head. My hair pushes them up and it falls off repeatedly. I honestly don't know if it's my hair, the shape /size of my head, or a combination of the two. But since becoming religious I've discovered I can only find Kippot that fit if I have a nearly shaved head. – Aaron Aug 18 '17 at 07:16
  • @DanF I think I'm just going to stop wearing a Kippah and use my tallit Gadol as a Kippah when I'm in the Beit K'nesset. – Aaron Aug 18 '17 at 07:16
  • You may want to ask your rav about using the tallit alone to cover your head. I'm not that familiar with the halachot regarding this. What would you use outside the Bet Knesset, the rest of the day? They do make knitted / crocheted kippot / caps. Some of them look like mesh "sacks". I'm not saying that they're "trendy" and look great on men, as many of them are designed for women. But, they may work for you if nothing else does. And, for all you know, you might start a new fashion trend. – DanF Aug 18 '17 at 13:30

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You can wear a beanie if you can get past the social hurdle of not fitting right in - there is nowhere specified that a Kippah must be worn! It's more of a unity and comfort thing.

The head shall be covered with whatever means necessary.

Ilja
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    "...If you can get past the social hurdle of not fitting right in" - Well in the Orthodox community having long hair is already against the grain. So he should have no problem there. – ezra Jul 02 '18 at 22:36
  • Pretty sure that this is a machlokes whether Kippa is an obligation or not. – DonielF Jul 02 '18 at 22:48
  • @DonielF Pretty sure it's just not an obligation. – Aaron Jul 03 '18 at 15:27
  • @Aaron Take a look at R’ Moshe regarding wearing a kippa to work - I don’t recall the exact place in Igros Moshe where he discusses it, but I’m almost positive that he brings down that it’s a machlokes between the Taz and the Mishnah Berurah but paskens like the Taz that it’s just a minhag. – DonielF Jul 03 '18 at 15:38
  • @Doniel This is a much bigger debate than between those two sources. But the standard Sepharadi p'sak is that it's minhag, albeit a strong one. – Aaron Jul 03 '18 at 15:45
  • I know it’s a much bigger debate. I know what the standard psakos are. But to say that this is straight up the Halacha is not so simple, without quoting the relevant psakos. – DonielF Jul 03 '18 at 17:07