Neither of my boys really mind t-shirts or sweaters. It's the pant outfits and shoes that they really haven't cared for....although they both have pjs on right now.
I try to find things that are easier to put on. Their hair can get tangled in velcro, zippers and around buttons so I try to be mindful in what I buy. Probably the easiest thing I've found to put on are what I call the horse blankets. You can just lay it on their back and it velcro's around their neck and then around their belly behind their front legs. I often use these when they have to go outside for quick potty trips in the cold. If they are ok wearing a harness, they probably wouldn't mind something like a horse blanket.
I never really had to break my boys into wearing clothes. They just never really minded wearing them. However, they aren't fans of getting dressed or undressed...especially when you have to pull a shirt over their head.
You'll probably want to supervise your pup at first to make sure it doesn't chew the clothes. |