I haven't attempted the double harness, but general advice I got when asking around for avoiding escapes was that where there's a will, there's a way for cats. I think the ultimate answer is to make sure you train them to see you or a carrier you always have nearby as a safe retreat. We didn't train that young enough so we only go on walks right in front of our home and when she does get spooked enough to escape, she at least knows to run back to our door.
cats
A place to talk about and post pictures of cats
From experience, I can say that if your cat is really determined to slip out, he absolutely will (cats are liquid, after all), so it's more about risk management: ensuring that the harness fits well, that he's used to it and feels comfortable in it, that the harness has positive associations for him ("harness = I get to go fun places! no harness = I'm stuck inside"), and that he's properly supervised while wearing it. The last one is especially important, because it includes doing your best so that your cat won't have reason to want to slip out. Once used to the harness, the main reason a cat will try to slip out is sudden fear that prompts their flight impulse, so you have to be aware of your surroundings and proactive at either removing him from fear-inducing situations before they arise (this means monitoring both your cat's vibes and the environment around you), or being ready to pick him up and put him somewhere secure or hold him tightly in the case of something sudden and unexpected (like a loud truck passing by). Not all cats have the temperament for going much farther than the backyard or around the block, and so knowing your cat's limits is also important.
As far as double-harnessing, I'd be worried that it would make the experience uncomfortable for him (and thus make him more prone to wanting to slip out). Generally if you can pick your cat up by the back of his harness and he doesn't fall out, it's probably as secure as you're going to get. I haven't used your brand of harness before, but it looks more secure than the strappy kind.
tl;dr: to prevent break-outs, as long as the harness is properly-fitted, the most important thing is to ensure your cat is comfortable and very used to the harness.
Addendum: after years of use, I have been very satisfied with the security of this harness: https://www.kittyholster.com/About-Us.html
The only downside is that because it's basically a vest, it makes cats more prone to overheating on hot days (but on the flip side, it probably helps keep them warmer on cold days). Also you may need to occasionally clean accumulated fur out of the Velcro, but that's easy enough to do.
I used one like this for initial training in the back yard. Cat still turned liquid and got out easily. I truly don’t think any harness is 100% with a cat.
I've had him in a harness for a few days at home and he's tolerating it really well! I just know that since he was used to free roaming he will bolt. It's not out of dislike for me or the house. He has followed me on so many walks and been so loyal and sweet. He's been in a donut for the last week and a half-ish and I think he's gotten used to having something on him. I just know that he will be able to slip out and run amok.
He's a very nice and gentle cat and I bet he'd acclimate well to harnessed walks but still be prone to slipping out, if that makes sense. Like he wouldn't hate it but he is athletic enough that if he's determined to go he can just go. I can't lose him again.
Going from free-roaming to leashed is going to be a challenge for you and your cat. Additional reinforcement (treats?) may be warranted. I wish you both the best!
I've used a harness to take my cat outside. I have not found a harness that can keep him locked in. He'll slip it if he wants to. So we only go out in the yard and if he slips the harness, we go back inside. Honestly, I think you'd need something that also hooks the back legs in order to keep a determined cat from getting out.
Is there a back leg harness that you know of?
I know my cat loves me and being home but all animals are unpredictable and I do fear he might wiggle out of it and if he does he'll be gone for days and I'll be distraught the entire time. I'm uncomfortable with the possibility of him wiggling out because he used to free roam and he was attacked by another animal. He would go outside for 1 or 2 hours but always come back regularly and when he was gone for a long time I was so scared.
It's selfish but I don't think I would be able to live with myself if he broke out of the harness and was gone again. I already thought he was dead because my neighbors found his collar along with clumps of fur, and I grieved him, and hated myself, and then he waltzed back in 2 pounds down with a limp and several abscesses. I can't take the chance of that happening again.