How do I teach my dog to wear clothes?

Desensitize them to putting the clothes on! You can do that in a very positive way by introducing them to the clothes and giving them a small treat; this way, every time you go to put the clothes on, you can slowly build up their comfortability with clothes. For instance, you might show the dog some boots and then give them a treat. The next step would be to hold the dog's paw up and give the dog a treat. From there, you would put the boot on, take it off right away, and give your dog a little treat. As you do this, you can build up to the point where your dog associates putting on the clothes with something really positive.