Q.The individual is asking how do we understand the ruling of the hadeeth related to lowering the bottom part of the thobe or that which is being worn below the waist below the ankle and the hadeeth of the Prophet (Sallaahu alayhi wa sallam) when he was dragging his thobe when he came out of the masjid or to pray salaatul khussoof.
A.The shaykh (hafiathahullAllaahu ta’alaa) mentioned there is no contradiction between the two hadeeths at all. You have a hadeeth where the Prophet Sallaahu alayhi wa sallam mentioned whoever does so (drags his lower garment below his ankle) out of pride, this person their lower part of their ankle is in the hellfire. So the shaykh mentioned it’s upon an individual to be careful of this punishment.
The shaykh (hafithahullAllaahu ta’alaa) mentioned you also have that which took place in the story of Abu Bakr (RadiAllaahu ta’aala anhu). That he would try his best to keep his izaar (lower garment) above his ankles. The shaykh mentioned Abu Bakr (RadiAllaahu ta’aala anhu) did not intend that his thobe was below his ankles; in fact he was trying to keep it up. An individual who intends and purposely wears his thobe or his lower garment below his ankles, then this is something forbidden. However, Abu Bakr (RadiAllaahu ta’aala anhu) he mentioned he tries to keep it up & the Prophet (Sallaahu alayhi wa sallam) said you are not from those individuals who purposely keep it lowered and you do not allow it to go low out of pride. So the shaykh mentioned (hafithuAllaahu ta’aala) the hadeeths they explain one another and if an individual wears his thobe or his lower pants above his ankles and it continues to fall down because of his belt and the loosening of his belt then he should try to keep it above and as long as he doesn’t intend for it to go below then it does not fall under the prohibition.
The shaykh (HafitahuAllaahu ta’aala) then continued to clarify saying the individual that does it out of pride, that is allows his garment to fall below his ankle out of pride. Then this individual would continue to be in the hellfire until the day of judgement.
Shaykh Saalih Muhammad al-Luhaydaan (May Allaah preserve him) (Kitaab-ut-Tawheed Class Q&A Session 02.02.13 Riyadh).