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A Parasha & Halacha Shiur by Rav Mordechai Lebhar
One of the most famous disagreements in Halacha is that of Rashi and Rabbenu Tam about the order of the Parashiyot in the Tefillin. This is already an older disagreement, cited in the Rambam’s Teshuvot (there are lengthy discussions as to what the other Rishonim hold).
According to Rashi they are placed in the order in which they are mentioned in the Torah: Kadesh, VeHaya Ki Yeviacha, Shema, VeHaya Im Shamoa. Whereas according to Rabbenu Tam they are placed with the VeHaya’s in the center, so: Kadesh, VeHaya Ki Yeviacha, VaHaya Im Shamoa and Shema.
The Tur writes that a G-d fearing Jew should wear both pairs but have in mind to only fulfill the Mitzvah with whichever Tefillin are the right ones, so as to not transgress Bal Tosif – adding on the Mitzvot. Maran adds that only if you are known and famous to be a pious Jew (Hassid), so it should not seem like haughtiness (Yohara). This was the general custom in previous generations.
However, in our days, Hacham Ovadia Yosef in one of his first Teshuvot writes that one may wear Rabbenu Tam’s Tefillin, as the Hida writes in Birke Yosef that had become the custom in his days [Some say that only if one wears them together it is a problem of haughtiness (Kav Naki).] Rav Elyashiv also said that in our days it has become common practice. One should at least try to wear them once in his life.
[The Kav Naki (Rav Kalifa B. Malka) counts even more possibilities of Tefillin, and devises a way to wear all of the types of Tefillin throughout the year, reserving Rabbenu Tam’s Tefillin for the day after Yom Kippur.] As to an unmarried Yeshiva student, Hacham Ben Tziyon writes that he shouldn’t wear, but Hacham Ovadia argues, provided that he will have pure thoughts.
According to the Mekubalim both Tefillin are true and thus they should be worn at the same time, if they fit. However, most wear Rashi first and Rabbenu Tam second.