Mum's dog, a jack russell mix has a Drizabone dog coat, wool lining but it's waterproof oilskin on the outside so she doesn't get wet. Would he wear something like that without tearing it off? You can also get Weatherbeeta dog rugs, like a horse rug but dog size.

Have you tried enticing him into the kennel with food? We used to feed our dog in his kennel so he got used to it. Or maybe putting an old sheet/blanket inside so it's not quite so hard to lay down in?

Failing that..if he chooses not to use it and gets wet and cold that's his fault..lol.