Question: When is the appropriate time to recite the “Shehecheyanu” blessing on a new garment, at the time of purchase or the first time one wears it? Similarly, must one recite this blessing for every new piece of clothing one purchases?
Answer: The Mishnah (Berachot 54a) teaches us that upon purchasing new garments, one should recite the blessing of “Shehecheyanu Ve’Kiyemanu Ve’Higianu La’Zeman Hazeh.”
Regarding when to recite this blessing, the Rashba writes that this blessing should be recited at the time of purchase and not when it is worn. Indeed, the Rosh writes that this blessing was enacted upon the joy one has at the time one purchases a new garment. Maran Ha’Shulchan Aruch (Chapter 223) rules in accordance with this opinion that the “Shehecheyanu” blessing should be recited at the time of a garment’s purchase and not the first time it is worn.
Nevertheless, several Acharonim write that the prevalent custom is not to recite this blessing at the time the garment is purchased, rather, it is recited the first time one wears the garment at which point one is truly happy. Hagaon Rabbeinu Yosef Haim rules likewise in his Ben Ish Hai (Parashat Re’eh, Section 1) as does Maran Rabbeinu Ovadia Yosef zt”l. Since the recitation of this blessing is contingent upon the prevalent custom, one should not change this custom and recite the blessing at the time of purchase; rather, one should recite the blessing the first time one wears the garment in accordance with the custom of the entire Jewish nation.
Regarding which garments one should recite the “Shehecheyanu” blessing upon, since the “Shehecheyanu” blessing was instituted upon one’s inner joy, one may only recite this blessing upon garments which usually bring joy to people. Additionally, in order to warrant this blessing, the garment must be innately important, as the Mishnah states that this blessing is recited upon “a new home or new garments” (although it is preferable not to recite this blessing upon a new home). We can infer that the garment must be important just as a house is. The great Tosafists derive from here that one should not recite the “Shehecheyanu” blessing upon insignificant garments such as shoes or socks. Similarly, one should certainly not recite this blessing upon undershirts and the like, for such garments are not significant enough to require the “Shehecheyanu” blessing to be recited. It is indeed the prevalent custom to recite the “Shehecheyanu” blessing only on important garments as opposed to shoes (refers to regular shoes which are not expensive and important in the individual’s eyes), socks, and the like.
Summary: One who purchases a new garment must recite the “Shehecheyanu” blessing. The prevalent custom is to recite this blessing the first time one wears the garment. One should not recite this blessing on garments that are not so significant such as undershirts or socks. Similarly, one should not recite this blessing upon shoes which are not so significant or expensive.