Kvod Rabenu Shlit’a, more questions. I wear two taalit ketanim, can I put them on and remove them together?
A. Even if it is not a widespread custom even amongst Tzaddikim to wear more than one Taalis Katan, nevertheless if one desires to do so there is no prohibition (of Baal Tosif) involved. It is well known that great Torah sages were accustomed to wear more than one Tallis Katan in order to fulfill the mitzva of Tzitzis more completely or extensively.
This applies whether one wears a Tallis Gadol and Tallis Katan at the same time, or wears two or more pairs of Tallis Katan’s simultaneously, and this is indeed the general tradition everywhere to wear a Tallis Katan and Tallis Gadol simultaneously during Davening.
Rabbi A. Bartfeld as revised by Horav Shlomo Miller, Horav Dovid Pam, Horav Aharon Miller and Horav Chanoch Ehrentreu and Horav Kalman Ochs Shlit’a