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Answer: Classically, people did not wear tallit and tefillin during Selichot – for a simple reason. The times for Selichot are after midnight or very early in the morning (see Shulchan Aruch, Orach Chayim 581:1), both times when one cannot put on tefillin. (We have written in the past about when it is preferred and permitted to recite Selichot.) Therefore, wearing tallit and tefillin could not be part and parcel of the halachot of Selichot, even when done after it is light in the morning. It is not proper, then, to miss some of the Selichot while putting them on first.
However, it is a good question whether it is a positive thing to try to have tallit and tefillin on for Selichot when possible. Selichot are a certain type of set of tefillot (see Rosh Hashana 17b), which overlap (especially for those who say Yud Gimmel Middot daily) with elements of our daily tefilla. Is there a connection between tefilla and tallit and tefillin? Let us take one at a time.
Married men wear a tallit at Shacharit. We have discussed in the past (it will soon be published in Living the Halachic Process vol. III, F-7) the reasons to wear a tallit at Shacharit considering that we already are wearing tzitzit and why these reasons are not important enough to have single men do so. One approach is that it is good to make sure we are wearing valid tzitzit (our "tzitzit" garment might be too small), which has special significance at Shacharit when we recite the Torah section on tzitzit (see Darchei Moshe 8:3). According to this, Selichot, in which we do not mention tzitzit, is not a time when a tallit is needed. Another possibility is that it is a good thing to cover one’s head with the tallit. According to this, perhaps there is a preference to have a tallit to cover one’s head during Selichot. On the other hand, why should this be more called for at Selichot than at Mincha, where we do not wear a tallit, unless we argue that since one is going to have it on for Shacharit, he might as well put it on prior to Selichot.
The Taz (OC 581:2) discusses the minhag for the chazan for Selichot to wear a tallit and the way to do it without needing a beracha, which one is not allowed to make at night. Since we recite the Yud Gimmel Middot, there is cause for the chazan to be properly cloaked, especially in light of the gemara (ibid.) that Moshe saw Hashem wrap Himself like a chazan when he taught Moshe how to do the Yud Gimmel Middot. Others discuss whether this is worthwhile, considering kabbalistic reasons not to put on tzitzit at night (see Beit David (Solonica) OC 9). All seem to assume that people other than the chazan do not wear a tallit. One could, on the other hand, argue that it is because of the problems of a tallit at night.
Shacharit is the chosen time for tefilin both because we need to wear them during the day in a state of cleanliness and pure thought and because they are mentioned in Kri’at Shema (see Berachot 14b). There is a connection, but a weak one, to tefilla (see Shulchan Aruch, OC 37:2). While one could say that the connection should apply to Selichot, we again note that it would not appear to be more important than at Mincha (there is an opinion that it is good to don tefillin at Mincha as well – see Be’ur Halacha 37:2, but that is clearly not common practice). Again, it is possible to argue that if we are putting tefillin on soon anyway, we might as well put them on for Selichot (as opposed to making one bring his tefillin with him for Mincha and put them on specially).
In summary, we have seen that it is not important to have tallit and tefillin on during Selichot. However, we raised the possibility, without succeeding to confirm or contradict, that there is some value in putting them on before Selichot. Therefore, whatever works practically for a person (including time and concentration considerations) is fine.
Bemare Habazak - Rabbis Questions (654)
Various Rabbis
147 - Kohen Seeking a Minyan With an Additional Kohen
148 - Tallit and Tefillin During Selichot
149 - Shortening Blowing of Teruah to Conform to Tekia
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Bemare Habazak - Rabbis Questions Ask the Rabbi: Forgot to Remove Tefillin Before Musaf of Rosh Chodesh
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
Rabbis in Midrash
Lessons
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.
Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.
Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.
