Monk's Hoody

[Ellie]

We could come out with a Monk Exclusive Hoodie item (Think uhm executioner's Hood) Like Mystra wears sometimes.

Only makes sense that a hoodie would mean you couldn't wear other headgear

For another example consider Giant Whisper Mask/Hat

We already know its possible for a headgear to override a sprite's head.
even Orc Ugly Face can do that.

Yes, but all of those completely remove the head. I would imagine that a hood would have to be supppperrr low in the face, or that your sprite would have to look bald/have a single chosen hair under it, as it would prove difficult to keep the custom hair under said hood.