Using an iPhone Charger and Case Excessively

I consider myself something of a secured person when it comes to caring for my hardware. Whether it's my cell phone or video game handheld, I always feel like I need to have something surrounding it so that it isn't bouncing in my pocket in an unprotected manner. An iPhone case, free from its iPhone charger, helps but at what point do you announce "this might be too much?" Protecting such items that you might find in an iPad dock is fine but at times the overprotective bug bites hard.