Which type of tzitzit should I buy? Guidance for tzitzit beginners

For those setting out to buy new tzitzit to wear, shopping for a tallit katan can be somewhat perplexing. First of all, the sizing system in Israel and the US are not the same, and many people have no idea what size they need, even if they have some tallit katans in their closet. Secondly, new tallit katan designs appear on the market fairly often, so choosing which type may be a decision to mull over.
The task can be a lot more challenging for those who are just starting to wear tzitzit. This week we received an inquiry from someone by the name of Craig from Manchester, who was overwhelmed trying to figure out whether he should be wool or cotton; and if cotton, a traditional tallit katan or undershirt tzitzit? And that’s before he even starts to consider the type of tzitzit strings and the sizing. The following is an email exchange with him, which other prospective tzitzit buyers might find helpful.
Craig: Hey! Must a kosher Tallit Katan be open at the sides?

It must be more open than closed. For example, if you measure the side, starting from the bottom, if it’s open for 16 inches until you hit the first stitch, and then it’s closed from that point up to the top for a length of 15 inches, then it’s kosher. This is a problem you sometimes come across with t-shirt and undershirt style tallit katan products. I have occasionally seen it with manufacturers under very observant ownership. Sometimes a whole production line can be okay except for one size.

Craig: It seems as though, according to Halacha, a Tallit Katan must be wool?

“Must” be wool – no. The question is whether it’s cotton if you are fulfilling the mitzvah on the Torah level, or the Rabbinical level (d’oreisa or d’rabanan). According to Sephardic poskim, only requires tzitzit according to Rabbinical law; the prevailing view among Ashkenazim poskim is that cotton requires tzitzit according to Torah law.
Craig: So even though a cotton Tallit Katan is deemed to be Rabbinically decreed rather than decreed by the written Torah, is it considered to be “less observant?”
If you’re Sephardic, then yes. If you’re Ashkenazi, then maybe you could make a case to say that. But the majority of Ashkenazim, including Orthodox and “ultra-Orthodox,” have no problem with cotton. Most people would consider a traditional cotton tallit katan “plenty observant.” The Vilna Gaon and the Chazon Ish wore cotton. I’d say you get into “less observant” when you wear an undershirt-style or t-shirt-style tallit katan. Among other things, according to some opinions, a tallit katan should not be worn directly on the skin.
Craig: I read the halacha regarding the wool/cotton debate for Tzitzit. What do you recommend?
This article might help (or might leave you more bewildered). Most people start with cotton.
Craig: What is your opinion? I am so confused and don’t know which one to go with! I have so many question, I could chat to you all day lol! I’m new to Judaism and am trying to figure all of these things out. Is it ok for the Tallit Katan to have sleeves (in the form of a T-shirt)?
According to all opinions it’s kosher, but according to some opinions it’s not ideal. I’ve never understood what the problem is.
Craig has yet to make a final decision. I hope I haven’t overwhelmed him with information. The truth is that buying a tallit katan can be very cut-and-dry — or quite complicated. Even those who have been wearing tzitzit for years might come across the halachas regarding the shiur beged (minimum size requirement) or exactly how to measure it properly (namely the issue of the T-neck opening). And of course some people are mulling a switch to techelet. So although tzitzit seems like an easy, straightforward mitzvah, there are actually numerous issues to address.