Is it recommended when already in Makkah to leave, reenter, and perform another ʿUmrah?

Shaykh Ibn Taymiyyah mentions that early Muslim scholars were agreed that such a practice is disliked. He said that performing ṭawāf is better. Majmūʿ al-Fatāwā 26/248 This practice was not followed by the Prophet or any of his Companions, even though they had many opportunities to do so. The only incident was when ʿĀishah asked permission to leave Makkah after she had performed Ḥajj so she could perform an ʿUmrah as well, but that was due to her special circumstances.

Allah knows best,

Imam Mustafa Umar

If I fly to Jeddah airport, which is within the mīqāt boundary, but then plan to go first to Madīnah, before proceeding to Makkah, must I wear the iḥrām?

If you enter the mīqāt boundary without having the intention to proceed to Makkah for ʿUmrah or Ḥajj, then it is not necessary to assume the iḥrām. Since your destination when landing in Jeddah was Madīnah and not Makkah, there is no need to put on iḥrām from that location, since Madīnah is outside of the mīqāt boundary.

Allah knows best,

Imam Mustafa Umar

Is it allowed to wear underwear or shorts under iḥrām clothing if I get painful chafing between my legs without it?

A pilgrim is not supposed to wear clothing which is sewn to cover the limbs, like a pant, shirt, or shorts. In order to avoid such discomfort or illness, anti-chafing cream or some other medical product may be used. If this does not suffice then it will be permissible to wear to the extent that it is needed to prevent hardship and illness.

Allah knows best,

Imam Mustafa Umar

I was told that male pilgrims are not allowed to wear stitched clothing when in iḥrām but I notice that the towels and sheets being sold are stitched at the hem.

The reality is that stitching is not what is prohibited but that a piece of cloth should not be stitched closed. The Prophet said that when a person is in iḥrām “He should not wear a shirt, nor a turban, nor pants, nor a cloak. He should not wear cloth that has been dyed with wors or saffron…” [Sahīh al-Bukhārī (134) and Sahīh Muslim (1177)] Scholars have derived from this ḥadīth that articles of clothing which are sewn together in order to wrap around parts of the body are prohibited, like pants and shirts. This is because a one piece ‘unstitched’ garment is humble and simple. Stitching up a tear in this garment, for example, is not prohibited. Neither is stitching a pocket into it. Shaykh Ibn Taymiyyah writes: ““If a pair of pants is cut open, it becomes the equivalent of a waistcloth. There is scholarly consensus that it can be wrapped around the waist and worn even when proper waistcloths are unavailable.” [Sharḥ al-ʿUmdah] Shaykh Ibn Taymiyyah: “That which is sewn or bound together for purposes other than to go around a limb – and are not sewn in the shape and size of a limb – can be worn. For instance, a pilgrim can wear a waistcloth or shoulder cloth that is sewn up or that has patches sewn into it. This is because the ruling only prohibits articles of clothing that are designed to fit the limbs of the body. The prohibited articles of clothing are those that are sewn into sleeves and other limb-covering features – the normal clothing that we wear.”

Allah knows best,

Imam Mustafa Umar