بسم الله الرحمن الرحيم
If a person wears cotton socks over leather socks, then the permissibility of masah will depend on whether the socks are thin or thick.
If the socks are so thin and light that by wiping (making masah) on the cotton socks the wetness of the hands reaches the leather socks, then doing masah on them will be sufficient.
If the socks are so thick that the effect of the masah does not reach the leather socks, as is the case of most regular socks, then while wearing those socks over the leather socks the masah will not be valid.
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للمفتي محمد أشرف الاشاعتي
Vol.1 Pg.180