Allaamah Shaikh Muhammad Zaahid Al-Kauthari says in his Maqaalaat: “Salaat with shoes will be valid if they are taahir (clean) and do not prevent placement of the base of the toes on the ground as this is of the completion of Sajdah as explained by Al-Khataabi and others. The shoes during the era of Nabi (Sallallahu alayhi wasallam) were soft (i.e. sandals with the toes exposed and free). On the contrary, the solid (firm/hard) shoes of this age do not allow the Musalli to perfect Sajdah in them. Furthermore the Musjid of Nabi (Sallallahu alayhi wasallam) was strewn with pebbles.......It was inconceivable for filth to be attached to the shoes of Nabi (Sallallahu alayhi wasallam), for he did not walk in filthy streets. The alleyways of Madinah were clean, devoid of filth as a result of the obedience of the Sahaabah to the command of Rasulullah (Sallallahu alayhi wasallam) to adopt total cleanliness in the homes and outside the houses, and to a greater extent the Homes of Allah (i.e. the Musaajid). Thus it was simple for one to walk without trampling on filth. Furthermore, the ground was sandy and soft preventing any splatter (of moisture)..........On the contrary, the roads and toilets of today -- it is not possible to completely avoid trampling on filth and being safe from splattering (of filthy water) on to shoes because the floors of toilets are firm (tiled, cemented). This is further aggravated when one stands to urinate in western style (high toilets and urinals) . It is authentically reported that on the occasion of the Conquest of Makkah, Nabi (Sallallahu alayhi wasallam) had removed his shoes for Salaat. Thus, this is the last of the two acts (i.e. with shoes and without shoes). The one who avers that wearing shoes (for Salaat) is Mustahab, i.e. when the conditions for permissibility are found, regards it as Mustahab because of opposition to the Yahood. But today the Ahl-eKitaab enter their temples and pray with their shoes. Therefore, opposing them is in removing the shoes, not in wearing them. The response of Anas (Radhiyallahu anhu), i.e. him saying ‘Yes’, to the question: ‘Did he perform Salaat with shoes?’, does not imply that Salaah With Shoes? this was always so. This has been explained in Sharh Muslim of Nawawi.........In fact, today it is regarded as evil mannerism to enter the Musaajid with shoes as mentioned by Nawawi and Al-Ubbi in Sharh Muslim, and Ali Qaari in Sharh Mishkaat, and Muqri in Fathul Muta-aal, and Al-Lakhnowi in Ghaayatul Maqaal, and Ibn Abi AsSijistaani in Munyatul Mufti, and Al-Hamawi in Al-Ashbaah. In fact for them there is a precedent in the Sahaabah (Radhiyallahu anhum).............. In fact, one should not enter the Musjid with the shoes taken off except that they are covered (e.g. in a packet, for it is disrespectful to walk in the Musjid with the shoes exposed in one’s hands).......In Kitaabul Umm, Imaam Shaafi’ said: ‘I prefer that one should not make Sajdah with shoes which prevent contact of the feet (toes) with the ground.”
at the outset, it is allowed in the Hanafi madh'hab as long as the shoes don't have najasah on them. it is also because a sound Hadith - if i remember well - from bukhari corroborating that RasulAllah saws prayed with shoes on. imam riDa in his fatawa mentions this and says it depends on `urf [prevalent practise]; where it is considered contrary to adab, it is makruh; like the subcontinent. inshaAllah, i will edit this post in the evening and add proper references. wallahu a`alam.
Salam, I was a few months ago in the situation where i had to stop at a sevice stop on the way to london for salah, with a couple of other brothers. The imam from us, who follows the wahhabified hanbali way of praying, led the salah with his trainers on. Now, i have recently been told that this is not allowed by the hanafi scholars, (and i know not the position of the other madhabs). Please comment if you have knowledge on this issue.