It turns out if you get all exquisite clothing and accessories in morrowind he will let you pass without answering the questions. However if youve joined the imperial legion theyll request you put on your uniform. But due to a programming error when you equip both the imperial legion cuirass or any other compatible ones alongside the exquisite robe and shirt it doesnt count you as having them all equipped. I usually start this quest chain early before joining the imperial legion to avoid this. Ive always hated the “cut from a certain cloth” questline though.