It would be cool in theory, but I don't think it would look good. I mean all quadrupeds, or pokemon that otherwise can't hold shit with their arms would have to things in their mouth, or in a silly string around their neck. Which would really just look silly.
Yeah, sure, Choice Scarf, Choice Specs, Assault Vest, King's Rock and so on would look awesome.
But things like Leftovers, Life Orb, berries, Charcoal and so on would just like wrong.
SO yeah, some pokémon/item combinations would look awesome, most would look awful. And lets not even talk about how much time it would take, for something relatively trivial. Time much better spent on other stuff.
