Benefits of Leather Socks: 
1) It is a Sunnah of Rasoolullah (s), 
2) Protects feet from diseases 
3) Protects feet from the cold, 
4) Prevents chipping and soreness, 
5) Keeps the feet dry which prevents bad odor. 

Method of doing Masah (Wiping): After wetting all the fingers of the hands they should be placed on the front side of the leather socks, keeping the palms apart and the fingers be drawn towards the ankles. If palms are also placed upon the leather socks and drawn with the fingers, it is also permitted. 
While on a journey it is permissible to do Masah for three days and three nights and if not on journey then for 24 hours. The day and night shall be counted from the time ablution is breached and not from the time when the leather socks were put on. 
If the leather socks are torn from several places and the total opening is equal to three fingers on the same sock, then Masah is not allowed, otherwise it is permissible.