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All of the button down shirts that I own cannot be rolled up past the elbow. To put on tefillin I need to roll the sleeve all the way to the shoulder. What do you look for in a shirt to determine that its sleeves will accommodate rolling so high?

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First of all, don't roll them up. The Mishnah Berurah and the Levush both write that, based on the language of the Pasuk, it is best to keep the Shel Yad covered.

Most button-down shirts have sleeves that can be unbuttoned at the wrist, raised past the bicep, and then brought back down over the Shel-Yad for re-buttoning at the wrist.

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    "don't roll them up": you have to roll them up when putting the shel yad on, no? And that's what the question says: "To put on tefillin I need to roll the sleeve all the way to the shoulder" (emphasis supplied). – msh210 Jan 6 '15 at 19:59
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    @msh210, based on the statement, "All of the button down shirts that I own cannot be rolled up past the elbow," I understood "roll" to mean actually roll, not just pull. When you roll your sleeves up, they tend to be tight around the arm. When you pull them up without rolling, assuming the wrist of the sleeve is unbuttoned, it tends to be looser fitting. – Seth J Jan 6 '15 at 20:16
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    @msh210, see: kosherimage.com/images/sweater01.jpg – Seth J Jan 6 '15 at 20:22
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    @msh210, my assumption is that he is rolling the sleeve up so that it actually stays up and doesn't flop back down and cover the Tefillin. I'm recommending that he abandon that attempt in favor of the opinion that the sleeve should cover the Shel Yad, which would help solve his problem (and may even make his problem moot). – Seth J Jan 6 '15 at 20:24

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