Join Date: Jun 2008
Location: SJ Newfoundland, Canada
Hmm, it can be tricky to make it a positive experience if they already have fears. Get a tighter fitting harness, as long as you can slip 2 finger under it it's fine, make it snug so when he gets smart he still cannot wiggle out of it. If you will be letting him out alone I suggest getting him a harness with a safety release clip on it in case it snags on something. They have become life savers in many cases.
If you will be walking him on the leash, well, good luck. Most cats will not walk like a dog so have some patience to just stand around while he nibbles on grass, chases bugs or climbs fences and trees. Do it a little bit at a time, and for gradually longer periods. Perhaps give him one of his favorite treats every now and then so he will accustom outdoors to good things.
If you prefer, get a large dog kennel, fence thing for yards and cover the top. Then kitty(s) can just go in there, harness free!