Before addressing the specific question, let us first consider when a man should begin wearing a tallis in general.
At first glance, we might assume that a man should begin wearing a tallis as soon as he is old enough to daven properly – as part of chinuch before Bar Mitzvah – and then as an obligation upon becoming Bar Mitzvah, as we find with other mitzvos. Why should wearing a tallis be specifically delayed until marriage? Where else do we find a mitzvah postponed until marriage when it can readily be fulfilled beforehand?
Indeed, this is the practice of Sephardim, German Jews, and some Hungarian communities: single men begin wearing a tallis at the ages described above. (See Likutey Maharich, Seder Mitzvas Tzitzis, s.v. ayen Be’er Heitev; Responsa Yechaveh Daas 4:2)
However, the minhag in many Eastern European communities, including Poland, Lithuania, and Galicia, is that only married men wear a tallis. What is the basis for this Ashkenazi practice, and what underlies the differing customs?
There are two primary sources that are central to understanding these opposing minhagim.
Several Rishonim write that single men do not don a tallis until they marry, based on the juxtaposition of two pesukim. The Torah states, “You shall make twisted threads on the four corners of your garment with which you cover yourself,” followed immediately by the pasuk, “If a man marries a wife” (Devarim 22:12–13). This derashah, juxtaposing the pesukim regarding tzitzis and marriage, serves as the basis for the custom of beginning to wear a tallis only after marriage. (Derashos Maharil, Hilchos Nissuin; Tashbetz Kattan 462; Rokeach 353)
Many Acharonim question the strength of this derashah for several reasons. First, it is not found in Chazal and therefore does not carry the authority of a derashah of Chazal. Second, it does not distinguish between a tallis gadol and a tallis katan; how are we to know which tallis it refers to? Third, if the pasuk refers to a tallis katan, would that mean that one should not wear tzitzis at all until marriage? (See Mishnah Berurah 8:9; Responsa Tzitz Eliezer 20:8; Responsa Rivevos Ephraim 5:19)
In light of these questions, many Acharonim maintain that this derashah is not sufficient reason to exempt a single man from wearing a tallis. This helps explain why Sephardim and some Ashkenazi communities maintain that a single man should wear one. Nevertheless, this derashah remains an important source for the widespread Ashkenazi custom of beginning to wear a tallis only after marriage.
The second critical source is the following Gemara:
“Rav Chisda would praise Rav Hamnuna to Rav Huna, saying that he was a great man. Rav Huna said to him: When he comes to you, send him to me. When Rav Hamnuna came before him, Rav Huna saw that he did not cover his head with a cloth, as Torah scholars did. Rav Huna said to him: What is the reason that you do not cover your head with a cloth? Rav Hamnuna said to him: The reason is that I am not married [and it was not customary for unmarried men to cover their heads with a cloth]. Rav Huna turned his face away from him in rebuke and said to him: See to it that you do not see my face until you marry.” (Kiddushin 29b)
The Magen Avraham understands this Gemara as evidence that a single man does not wear a tallis. (Magen Avraham 8:3, cited by Mishnah Berurah 8:4) Other Acharonim, however, disagree. They understand the Gemara as referring not to a tallis, but to a separate practice among Torah scholars of covering their heads as an expression of modesty. According to this interpretation, the Gemara provides no evidence that a single man should refrain from wearing a tallis. (Be’er Heitev 8:4; Mor U’Ketziah, ad loc.)
Thus, according to the Magen Avraham, one of the most important Ashkenazi halachic authorities, a single man should not wear a tallis. His interpretation, however, is challenged by other leading Ashkenazi authorities.
To summarize, the Sephardic practice is for a single man to wear a tallis, and this custom has significant support in Shas and the Poskim. The widespread Ashkenazi practice is for a single man not to wear a tallis until marriage, based on the derashah cited by the Rishonim and the interpretation of the Magen Avraham. Other Ashkenazi authorities, however, support the practice of single men wearing a tallis for the reasons outlined above.
We can now return to our original question: May a single man wear a tallis if he is embarrassed not to wear one?
Certainly, a Sephardic man, or an Ashkenazi man whose family custom is to wear a tallis before marriage, should do so. The question therefore applies specifically to an Ashkenazi man whose family and communal custom is not to wear a tallis before marriage.
On the one hand, the importance of preserving an established family and communal minhag should not be minimized. Minhag avoseinu b’yadeinu teaches that customs should not simply be changed because of discomfort, personal preference, or a change in attitude.
On the other hand, embarrassment is a reality that Halachah takes into consideration in a variety of circumstances, and halachic authorities discuss when it may factor into halachic decision-making. In this case, because there is significant halachic basis for wearing a tallis before marriage even within Ashkenazi sources, there is room to argue that an Ashkenazi man whose custom is not to wear a tallis before marriage may nevertheless begin wearing one when refraining from doing so causes him significant embarrassment.
Ultimately, balancing the importance of preserving a family and communal minhag against the genuine embarrassment an individual may experience is a serious and sensitive halachic question. It should therefore be discussed with one’s Rav, who can evaluate both the halachic considerations and the particular emotional circumstances of the person asking the question.
