I would recommend that you try let your cat wear clothes 1 hour each day and give him a nibbly treats afterwards until he is very comfortable with clothes. Be very quick in putting clothing on him. Put the clothing over his head really quick and be gentle and quick when putting his forepaws through the armholes. A little complaint meowing is ok, but I would stop if he hisses and starts to scratch.
Some cats like to wear clothes because they instinctively know they look cute in them (like Pepper). Others wear them to please their owners and like the attention they lavish on them. Still others like the warm comfortable feeling of clothes.
Pepper took to wearing a sweater no problem sitting still but started walking funny when he first started wearing his sweater. But after about a week of wearing it he is walking naturally. Oh yes on a frosty January, -20 Celcius day, I made Pepper wear his sweater outside, and when he came back he even gave me kisses as to say, "Thank you for making me that sweater and help me keep warm!"
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