Where does the minhag of not cutting a boy’s hair till 3 years old come from?

Answer:

The custom of not cutting a boy’s hair until the age of three is mentioned by Arizal (Shaar Ha-Kavanos 87a), and is generally seen as being related to the mitzvah of leaving the pe’os ha-rosh, in bringing the child to love the mitzvah (Nechpah Bekesef p. 18). Some add that the three year delay is related to the mitzvah of orlah, and indicates a certain spiritual readiness (Ayalah Shluchah) — according to one Midrash Avraham was three when he discovered Hashem. In any case, the custom is fairly widespread, though it is not mentioned in rulings of halachic works, and some have the custom to cut hair earlier (such as Skver, where the custom is two years old).

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