It's not too late to winterize your dogs by getting them used to wearing boots and jackets. Many of my clients tell me that they would use them if their dog would just keep them on. Don't relent! Before you introduce the boots, massage your dogs feet for a week or so every day, so they are used to being touched there. This may take time for some dogs. Use treats while you are doing the massaging. Give lot's of affection while the feet are being massaged. Parallel with the massaging, keep the boots by your dog's food dish while they are eating so they can see the boots as a positive "friend".
Make the actual putting on of the boots to the dog's feet a pleasant experience by taking your time, being patient, deep breathing if necessary and then rewarding with treats and affection when the boots are on them. Just walk your dog around the house on leash slowly at first and only for short periods of time. These walking sessions can be as short as 2 minutes. If the dog can't figure out how to walk in them, just let him stand. It may take a while for him to get used to the feeling of the foreign objects. In time, you can progress outside. Don't expect too much of a dog that balks at having boots on their feet. Take it slow and don't take no for an answer. Reward them when they do it correctly and not for inappropriate behavior.
You may contact me on the Contact page form if you have any questions or could use some assist with this.
Good Success to you,