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If he is going to escape, I am not sure because each situation / cat is different, he maybe able to with the shirt as well. You need to get a harness that fits properly and that is tight enough. I used a small dog harness for my kitties since they escaped from all of the cat harnesses I tried.If I buy him like a shirt or a sweatshirt and put it over the harness do you think he would be able to Houdini himself out of the harness and treats should work I tried this with spooky she went nuts
He needs to wear it inside for a while and you can try walking him inside to see how it goes. Some cats are probably too skittish to be walked outside, they may get too excited, especially if they have never been outside.