the first time i put a sweater on nala i had two friends over and my friends yorkie and she went nuts, acting like she couldn't walk, kept falling over it was pretty funny. then one day while she was chewing on a greenie i put it on her again and she acted fine like she didn't really notice. too bad by the time i got it on her it didn't fit!! maybe try putting it on him while he's not paying attention or sleepy