Halakhic Positions of Rav Joseph B. Soloveitchik by R. Aharon Ziegler
We tend to look askance at someone wearing Tefillin in the afternoon. To most of us, it’s a strange sight and we wonder why that person had not donned his Tefillin in the morning like the rest of us. It does not occur to us that the person might indeed have put them on in the proper time of the morning hours but he harbors a need to wear them all day long. Is that really wrong or is it perhaps meritorious to wear them all day long?
From the Gemara Menachot it certainly appears that the Amora’im wore their Tefillin all day long. The Gemara asks (36a), “Until when may one wear his Tefillin?” And the answer of the First Tanna is, “until the sun [finishes] setting”, R’ Ya’akov states, “he may leave the Tefillin on until pedestrians have vanished from the market”, and the Chachamim state, “until the time of sleeping”. Furthermore, the Rambam states explicitly (Hilchot Tefillin 4:25), that the Kedusha of Tefillin is so great, that as long as one wears them on the head and arm, his personality will remain humble and G-d fearing. Therefore, one should make every effort to wear them all day long, for that is indeed the proper Mitzvah. And then the Rambam adds, that it is told about Rav, the disciple of Rabbeinu HaKadosh that all his life no-one saw him walking four Amot without Torah, without Tzitzit, or without Tefillin. Then Rambam concludes, although it is meritorious to wear Tefillin all day there is a special Mitzvah to wear them during Tefillah.
Rav Soloveitchik analyzed this Mitzvah by stating that from the perspective of simply fulfilling the Mitzvah of binding the Tefillin, as found in Devarim 6:8. “U’KESHARTAM LE’OT AL YADECHA VE’HAYU LETOTAFOT BEIN EINECHA” (You should bind them as a sign upon your arm and let them be ornaments between your eyes), one fulfills that aspect of the Mitzvah by merely donning them for a few minutes a day. However, from the perspective of the Gavrah, the person, the effect and Kedusha that the Tefillin have and leave upon the person that aspect of the Mitzvah deserves a greater length of time, and wearing them all day long is not hard to understand. Tefillin is the only Mitzvah of the Torah that even the non-Jewish world will look upon us with awe and respect, as the Torah states, “Then all the people of the earth will see that the Name of HaShem is proclaimed upon you and they will revere you” (Devarim 28:10). So, although it is not our minhag to wear the Tefillin all day, nevertheless, the concept of doing so is certainly a meritorious one.
From Torah Musings, here.