I agree that if a dog does not like to be dressed up you should not dress them up. I, however, also agree that if putting a doggie sweater on your Pup will keep them warm, healthy, and happy you should do it. Lets face it not all dogs were meant to be in the colder climates even though their owners may take them there.
Both of my dogs get the occational outfit. Neither gets them all day everyday but they do get them when mainly they want them. Our big dog who loves being outside and playing rarely wears a sweater but will try to put a sweater on himself. Our little dog has actually put his sweater on himself. I know I have crazy but lovable puppies.
Just my thoughts on this matter as well