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1

I think the distinction is how and when the item is functioning. The shepherd's sackcloth raincoat is functioning as a garment when worn over the body (e.g. by protecting from the rain). For a woman, a signet ring has no aesthetic value when worn and wearing it is just a way to get it from point A to point B.


2

Shepherds do not merely carry sacks, they use sacks as clothing/adornments by using them as raincoats, as Rashi indicates (see ד"ה בשקין and אלא). Women do not wear signet rings as clothing/adornments, period. R. Yirmiah is simply observing that when women occasionally carry signet rings, they do so by wearing them on their fingers. Therefore, while signet ...



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