He assumed Ihram while wearing Underpants intentionally
Question :
At the Miqat I made intention to assume Ihram for Umrah joining it as a Mutamatti' with Hajj. However, I did not remove my underclothes (underpants). This was due to the extreme shyness I felt during that time. I performed the 'Umrah in Ihram while I was wearing the underpants. When putting on the Ihram clothes for Hajj, I knew that I was doing something wrong by wearing underpants, so I removed them during my assuming Ihram to perform Hajj. My question is, is there any sin on me for not removing my underpants only for performing Umrah, even though I removed them for the performance of Hajj? This occurred while I knew that seamed garments are from those things that nullify the Ihram. However, the reason I did this, as I told you, was my extreme shyness during the first time I performed 'Umrah and Hajj. Since this 'Umrah and Hajj of mine happened a number of years ago, I would like a beneficial answer.
Answer:
You are obligated to make a ransom of atonement for intentionally remaining in these clothes while you knew that it was one of the things prohibited for Ihram. However, it is not of those things that nullify Ihram. The ransom is to fast three days or feed six poor people or slaughter a sheep. Which ever of these you do, will suffice you. However, the slaughter or feeding people must be done in Makkah for the poor people of the Haram. In reference to fasting, it is correct to do it anywhere. There is no sin on you for delaying, except that you were negligent in not asking for this long period of time.
Source:
Ash-Shaykh Ibn Jibreen
Fatawa Islamiyah, Vol. 4 Pages 142-143