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There is a law in the torah (and the meforshiim afterwards) to attach tzitzit to all four cornered garments that you will wear.

Ok. I understand that.

But where did it come to pass that some people say one is required to wear tzitzit?

If I am not wearing a four corned garment, why should I go out of my way to acquire one?

Is it a halachic obligation to? or is this just custom?

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Very, very strong custom and halachic preference. Gemara says someone who wheedles his way out of a mitzva (e.g. by actively rounding the corners of his garment) is someone who, when Hashem gets angry, well watch out. More here. And specifically about tzitzis, here.

It's such an easy mitzva to do that why avoid it? Standard Jewish practice has become long ago to give ourselves the opportunity for one more mitzva.

Shortly before his death the Vilna Gaon cried that a mitzva like tzitzis only takes a couple of kopeks (well dollars today), but once we pass on there are no more chances to do mitzvahs.

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The Gemara is talking about doing something active (as you say, rounding the corners of your garment) to get out of performing a mitzvah. Naftali is asking about our situation today, where all of our clothing comes pre-made without any corners at all. Must one go out of his way to acquire a special undershirt with corners, just so he can affix tzitzis to them? – user1095 Dec 19 '11 at 15:33
"It's such an easy mitzva to do that why avoid it?" Again, avoidance implies action (like modifying existing clothing to exempt it from needing tzitzis). This is merely "shev, v'al taaseh". A Jewish man who wears modern day clothing with no corners on it, violates nothing by not going out and buying a strange looking undershirt, just to have something that needs tzitzis. – user1095 Dec 19 '11 at 16:14
Minhag. Shel. Yisrael. – Shalom Dec 19 '11 at 16:41
Some argue that wearing an Italian black felt hat is "minhag Yisrael" Others would tell you that speaking Yiddish qualifies. The question asks "Is it a halachic obligation to [wear tzitzis undershirt]? or is this just custom?" I'm saying it's not a halachic obligation. You come back with, it's a custom. Can you admit, to answer the question, that there is no "halahic preference" to wear the undershirt? – user1095 Dec 19 '11 at 17:08
@Will. This minhag is in Shulchan Aruch and has been accepted by the entire observant population. That has halachic force. There still remains a halachic preference as well -- just as there is the "halachic preference" to do as many mitzvahs as we can. – Shalom Dec 19 '11 at 17:42

Lechatehila one should always Tzitzit (Shulhan Aruch 24:1). The language Maran uses is "Tov" meaning Lechatehila (see Emet LeYaakov of HaRav Yaakov Peretz Shelit"a).

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I think the logic is "if you can, then why not?" I don't see why anyone today shouldn't wear it. If you are embarrassed then there is Deot that say you can tuck it in (although Lechatehila, according to Sephardadim and Ashkenazim they should be exposed). If it is dangerous tuck them in. If you playing sports, you certainly can remove them. Why not do a mitzva if possible? I heard in the name of the Alshich HaQadosh that once someone puts on the Talit they are performing 613 Miswot. So why not wear Tzitzit? If you can, the Yalkut Yosef says (siman 8 I believe) that if one can and he doesn't there is a big Onesh involved. So just do it. It is also a protection, as we learned in Masechet Shabbat. There are many benefits in wearing Tzitzit.

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Menachos 41a says that someone who doesn't go out of his way to wear tzitzis may be punished DURING TIMES OF DIVINE WRATH. So, if you live under threat of pogrom, or anti-semitic fascism, or the most anti-Israel Pres.... ....alright everyone, let's put on those undershirts!!! :) – user1095 Dec 19 '11 at 17:15
All kidding aside, we are blessed to live in a time of peace and prosperity for the Jewish people, this is certainly not a time of Divine Wrath, so it seems that today, someone who chooses not to wear a special four-cornered undershirt receives no punishment at all. – user1095 Dec 19 '11 at 17:17

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