Dennis in the beginning was horrible to dress, he would have it in his mouth biting and tearing at it before I could get it over his head. It was very frustrating! However when I did manage to get the shirt on he enjoyed it, so much so that he is very excited and can hardly wait for me to put one on him now. It just takes awhile for them to not only understand it but to really enjoy it. My friend has a Boston Terrier and whenever he is ready to go outside he insists on having his boots and coat put on. He is too funny!
Also if you are talking about a coat or jacket, sometimes they can be a little tight and inhibiting, so maybe just try t-shirts, which are much more comfortable. I think he will come around.
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