When my sons’ hair got to be too long, in both cases I put the hair in a ponytail then put it up and placed a yarmulke over it, clipping it on all sides. It kept the hair under the kippah, it kept the kippah on the head, and my sons got used to having their heads covered at all times from about the age of 18 months. They never tried to remove the yarmulkes. I put it on them the first few times while they were napping in the stroller, and they got used to it immediately, till it was second nature to have it on. You have to be careful and very watchful with the clips, as they can be a choking hazard. They had not yet invented the KIPPON velcro strips when my boys were little, so maybe those are the best thing to use to keep them in place nowadays.
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