I'm in a middle of checking out gear use in Teemu. At first my plan was to remove items from inventory when they are in use, but then I went back to "Nethack" style where the item tells what use it's in. The difference is that you can do stuff like throw away your weapon and then you need to check out if it was part of a wardrobe etc. It's not as complicated as it seems, because you "only" need to check this in routines that discard items or change armour etc.
This falls in a category of "thinking everything" which sometimes is a part of roguelike programming. Rather than trying to understand how the code works you practically have to try out everything and see what happens. In Teemu it's even possible to eat away your armour. Creating a system like this can be both fun and a bit challenging, but I think it fits better in the style of this game.