My little Miloh often wears shirts, primarily because he recently got a "summer cut" (very short) haircut and only weighs 2.8 lbs right now; he gets really cold easily. He actually has no problem wearing clothes, I guess he's gotten used to it.
I have heard "smart" comments from my boyfriend's family, like "You treat that dog like a dang child when he's just a dog, why don't you just have one already?" I often laugh it off but there have been times I have to keep myself quiet.
But it all depends on the individidual and of course the adorable yorkie.