He may and may not - try leaving on something a little each day ...& maybe distracting him too will help - but if he hates clothes that much - let him be NEKKID :
my girls knew they looked too cute and ate up the attention from the 1st time of wearing clothes...
I think the funniest thing I ever read was the dog who (when wearing his first sweater) - just fell over to his side and wouldn't move - I would NOT dress a dog who felt
that bad wearing clothes