I'm having a problem with rigging clothes on Blender.

Right now, I'm animating a hand with a gun (which I'm also having a problem with, I've made a topic on that).

The problems I'm having with clothes are that when I try to move the armature, the clothes either don't band/deform as much as the model itself, or it does it too much, and no matter how much I tinker with weight paint, it doesn't make a difference.

I've tried looking it up on Google and Youtube, and found no tutorials on actually rigging clothes with a model.

What do I do? I feel like I'm going to tear our my hair in frustration any minute now!