Last week I got my healer boots from WoD. They are great for my WHM, so I decided to use those, but I had to glamour them over with the Emperor's new boots to keep the look I wanted. Because I really like the look of the WoD set, I decided to give that to my SCH, but when I tried to glamour my SCH's daystar boots with the WoD ones, it wouldn't let me because Glamour can't stack. Is there any way around this?

Basically:
WHM -> WoD boots, look like Emperor
SCH -> Daystar boots, look like WoD boots

I've been told that you don't need the item in your inventory after you glamour it, so if I gave my glamoured pair of WoD boots to a retainer and got another pair to glamour over the Daystar boots, would the glamour still show up if I discarded/give my retainer the second pair of WoD boots?

I hope it makes sense.