I totally understand what you are saying being from Montreal, Quebec myself.
I have a Lhasa Apso who can't take walking on the cold ground either, especially now that he is older. I started to put winter boots on him when he was about 7 or 8 years old and had no problem with them. Believe me though, when I first put them on him, I thought that they weren't going to work because he couldn't walk in them properly while in the house, but when I got him outside and on the sidewalk, he walked just fine in them. You have to make sure that the boots are the right size for your dog and that the dogs toes are right at the end of the boot. You have to pull them on like you would when you put your socks on. Also the straps have to be tight enough so the boot won't slip off. Don't give up okay. Your little dog will thank you for keeping his little paws warm. Also, get a little winter jacket to put on him too. Just because an animal has fur, it doesn't mean they don't get cold.
Good luck with the boots.

Also, you really should have put your thread in Dog General. You would have gotten a better response to this problem.