– Q. As the cold days of winter are approaching, I often fill that I should use an extra t-shirt to keep me warm. If instead I use another Talit Kattan, will I comply with a double mitzva if I’m already wearing one? Do I have to say another bracha when I put on the second one? What about someone already wearing a Ta’alit, but it is cold in shul and he wants to use also his weekday Ta’alit on top, does he have to make another bracha?

A. Indeed, one complies an additional mitzva with every Taalis Kotton or Godol one wears.
It is well known that HoRav Chaim Pinchas Scheinberg zt’l – Rosh Yeshiva of Tora Ore, wore many sets of tzitzis at the same time, (some mention even 150 others mention even more).

If one wants to wear additional sets, if he did not have in mind at the time he recited the brocho the first time he must make an additional blessing.
Horav Shlomo Miller’s Shlit”a opinion is similar.

Rabbi A. Bartfeld as revised by, Horav Dovid Pam, Horav Aharon Miller, Horav Chanoch Ehrentreu and Horav Kalman Ochs Shlit’a