In The Name of Allaah, The Most Merciful, The Bestower of Mercy.

A man from the companions of the Prophet [peace and blessings of Allaah be upon him] travelled to Fadaalah Ibn Ubayd [may Allaah be pleased with him] when he was in Egypt. He came to him and said, “I have not come to visit you, but you and I heard a Prophetic narration from Allaah’s Messenger [peace and blessings of Allaah be upon him]. I hope you may have some knowledge about it”. He asked, “What is it?” He replied, “Such and such”. He said, “Why do I see you dishevelled when you are the ruler of this land?” He said, “Allaah’s Messenger [peace and blessings of Allaah be upon him] forbade us from indulging in excess luxury”. He said, “Why do I see you unshod?” He replied, “The Prophet [peace and blessings of Allaah be upon him] used to command us to be barefooted at times”. [Ref 1]

Al-Manaawee [may Allaah have mercy upon him] said:

If a person’s feet are safe from coming into contact with impurities, such as when he is on a sandy ground and it does not harm him, then it is recommended that sometimes one walks barefooted with the intention of taming and disciplining the soul. And because of this, it has been reported that the Prophet [peace and blessings of Allaah be upon him] used to walk barefooted at times and sometimes whilst wearing shoes, and the companions used to walk barefooted sometimes and whilst wearing shoes at other times. [Ref 2]

Imaam Muhammad Ibn Saaleh Al-Uthaymeen [may Allaah have mercy upon him] said:

It is Sunnah to wear shoes and it is also Sunnah to be barefooted. This is why the Prophet [peace and blessings of Allaah be upon him] forbade a person from wearing shows always and commanded that one walks barefooted sometimes. Therefore, the Sunnah is that there is no problem in wearing shoes, but it is befitting that sometimes he is barefooted amongst the people, so that this Sunnah is manifested, which used to be criticised by some people – when they see a person walking barefooted who say, “What is this?” This [objection] is wrong because the Prophet [peace and blessings of Allaah be upon him] used to forbid one from wearing shoes too much and commanded that one is barefooted sometimes. [Ref 3]

Al -Allaamah Abdul Muhsin Al-Abbaad [may Allaah preserve him] said:

If there are things on the ground that requires that a person wear shoes, then one wears shoes. For example, if there is glass, metal, stones or thorns on the ground or the ground is very hot due to the heat of the sun, then utilises this blessing which Allaah has bestowed on him and that is to wear shoes. However, the fact that sometimes he does not wear shows is due to what has been reported in this Prophetic narration from Fadaalah Ibn Ubayd [may Allaah be pleased with him]- that the Prophet [peace and blessings of Allaah be upon him] commanded them to be barefooted sometimes, so that there is no excess and exaggerated enjoyment, but rather a person appears a bit dishevelled (sometimes), but not always and forever, rather only sometimes. [Ref 4]

Ref 1: Abu Dawud. Number 4160]

[Ref 2: An Excerpt from Faydul Qadeer 1/317. Slightly paraphrased]

[Ref 3: Riyaadus Saaliheen 6/387. Slightly paraphrased ]

[Ref 4: Sharh Sunan Abee Daawud. 23/273. Slightly paraphrased]