Answer: The Shulchan Aruch (OC
37:3) writes that a boy’s father must buy him tefillin
when he’s mature enough to control himself and treat them with the proper
respect. R’ Ovadia Yosef (Yabia Omer OC 6:3; Yechave Daas 2:4) demonstrates
that this is the sefardi minhag (See Ohr Letzion 2:44:47)
While the Rema disagrees, writing that he must wait
until he’s bar mitzva, the Magen Avraham (37:4)
and Shulchan Aruch Harav (OC 37:3) write that the minhag
is for boys to start wearing them two or three months before their bar mitzva. Thus, minhag chabad is for boys to begin
wearing tefillin two months before their bar mitzva.
The Aruch Hashulchan (OC 37:4) notes that the minhag ashkenaz is to begin one month
before one’s bar mitzva.
R’ Eliezer Waldenberg (Tzitz Eliezer 13:10:3) notes that this is the minhag ashkenaz in Yerushalayim. He adds that even though they are
doing so to train themselves for when they are bar mitzva, they
should still say a beracha.
R’ Waldenberg later (ibid. 13:24:5) writes that one
who who wears them in advance of his bar mitzva doesn’t
recite shehecheyanu as when he first wears
them, he does so to train for when he is bar mitzva
and later on they are no longer new. Yet, the Chasam Sofer (OC 55) suggests
that a bar mitzva boy recites shehecheyanu when he wears his tefillin for the mitzvos that he is now obligated.
As there is a doubt as to whether one should say shehecheyanu or not, the Mishna Berura
(Biur Halacha 22:1) recommends that one wears new clothing then so that one
says shehecheyanu on both simultaneously.
Similarly, R’ Shlomo Zalman Auerbach (Halichos Shlomo 4:14) ensured that while
his sons began wearing tefillin
a month before their bar mitzva,
he didn’t gift them their tefillin
until the day of their bar mitzva so
that they could say shehecheyanu
then.
In conclusion, the main ashkenazi
custom is for boys to begin wearing their tefillin
for a month before their bar mitzva
with a beracha. Ideally, they should wear
a new suit on their bar mitzva
and recite shehecheyanu when they put on their tefillin.
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