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How do I wear tzitzit out with a tucked-in shirt? Do I need especially long tzitzit or some other trick?

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I think that you answered your own question. You either need long tzitzit or a short shirt. I can't think of any other methodm unless you want to wear the entire tzitzit "beged" over the shirt, which some people do. If that concerns you, you can always wear a jacket over it. – DanF May 16 '14 at 19:43
Would it make life easier for you if the knots were tucked in? (As is brought in halacha that they should be) – Y ez May 16 '14 at 20:41
I wear them in, but once I tried to emulate the rabbonim and couldn't get it to work on my tzitzit. – Clint Eastwood May 16 '14 at 22:04
epic question :) – bondonk May 17 '14 at 21:17

People normally wear their tzitzis out on the sides. Dress shirts are typically shorter there than in the front and back. It should be possible to use normal-length tzitzis and a normal-sized shirt together.

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Tragic mistake, as the Tzitzis are supposed to surround you on "all 4 sides"; 2 in front and 2 behind. (At least that's how it was the last time I checked in the Sh. A.) – Danny Schoemann May 18 '14 at 7:34
@DannySchoemann, most people I see wearing tzitzis out on purpose do so as I described. Perhaps the front ones are slightly front of center and the rear ones are slightly aft. – msh210 May 18 '14 at 7:36
@DannySchoemann I noticed early on that I could spot at a glance if a person is a baal tshuva or "frum from birth". BTs wear their tzitzis "spead out" to the "four sides", FFBs wear the right ones together, and the left ones together. :-) – Adám May 18 '14 at 13:05
@NBZ there must be a lot of Ba'alei Teshuvah in Williamsburg Brooklyn then (there are not) as they don't wear them the way you described FFBs as wearing them. Ed. oops, they also wear the beged over the shirt. Never mind... – Ploni Almoni May 18 '14 at 17:26
@DannySchoemann I believe "surrounded on all 4 sides" is understood to be referring to the garment, not the strings. Which is best accomplished with each side together, so that the garment completely surrounds your torso. – Y ez May 18 '14 at 19:39

From personal experience:

I use a Chzon-Ish size begged - about 120cm x 60 cm.

Leave the Tzitzis hanging out where you want them - and then tuck in your shirt around them. The front and back will be tucked in properly, the sides slightly less so.

BTW: According to the Tur (as quoted by the Aruch HaShulchan 8:10) you are not Yotzei the Mitzva of Tzitzis unless you have the strings on all your 4 sides; 2 in front and 2​​​​​ behind. He learns this out from the Pasuk על ארבע כנפות כסותך

והיינו דעיקר מצות ציצית הוא שיהיו שני ציצית לפניו ושנים לאחריו, כדי שיהיה מסובב במצות (טור). ונראה דזהו לעיכובא, דהא ''על ארבע כנפות כסותך'' כתיב, והכנפות הם שתים לפניהם ושתים לאחריהם.

The Shulchan Aruch in 8:4 similarly says:

מַחֲזִיר שְׁתֵּי צִיצִיּוֹת לְפָנָיו וּשְׁתַּיִם לַאֲחוֹרָיו כְּדֵי שֶׁיְּהֵא מְסוֹבָב בְּמִצְוֹת.

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And if you wear a jacket, any lack of neatness at the sides will be hidden anyway. (Thanks -- I'd wondered how people did this.) – Monica Cellio May 19 '14 at 13:29

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