Wearing Tefillin in the Street
Question:
I learned in the Mishna Berura that one should put on one's tallis and tefillin at home and then walk to shul. The Mechaber, Ramo and M.B. are all in agreement that this is the mitzva min hamuvchar. The only heter they mention for not doing it is if one were going to walk through filthy areas or crowds of non-Jews—neither of which would seem to apply in a place like RBS. Yet I very rarely see anyone put this halacha into practice!
Is there a specific reason why people don't usually do this, or is it just a habit from the Diaspora that we haven't yet broken?
Answer:
Your analysis seems to be correct in every way.
Apparently, the custom was for people to walk to shul with their tefillin on. Both the Beis Yosef and the Ramo say this was the prevalent custom in their communities. Ashkenazim would wear a tallis in addition to the tefillin. The custom does not seem to be halachic in nature; rather, it seems to have a mystical origin, based on the Zohar and minhagei Ha'Ari.
Nowadays the practice is practically non-existent. Quite likely, since the time of the Ramo, many Jewish communities found it impossible to follow due to rising anti-Semitism. The custom does not seem to have been re-established when the factors preventing its practice were no longer relevant.
Someone who initiates such behavior might be viewed as arrogant and flaunting his holiness. The fact that pretentious actions are immodest and therefore inappropriate further reduces the chances that the custom will be revived.
In some communities, it is more common for people to walk the streets in tefillin than it is in RBS. You may notice some people who are careful to don their tefillin in a side room before entering the beis midrash. This is in accordance with the modified custom of putting on tallis and tefillin in the shul courtyard when the prevalence of gentiles precludes wearing them in the street (M.B. 25:10).
BookID: 1 Chapter: 25