Is it permissible to wipe over socks to make things easier for oneself and abandon obsessive thoughts, or to follow one's family and not contradict the people, especially since Shafi'i stipulates that they must be "soled" – and what is meant by that – and is it permissible to wipe over thick winter socks?

It is permissible to wipe over socks (khuffs), and this is the madhhab of Imam Ahmad, and a group of Companions held this view. Its permissibility is indicated by a hadith narrated by Tirmidhi. The common person (layman) is allowed to follow someone whose knowledge he trusts. The person suffering from obsessive doubts (waswasa) in particular is permitted to adopt the easier opinions to remove hardship and دفعًا للمشقة (alleviate difficulty). It is not a condition that the socks be reinforced with leather (mun'alayn); rather, one can wipe over socks made of wool, cotton, and other materials.