I think it is a fine line between having fun dressing up your dog and going overboard. I think there are many owners that enjoy dressing up their dogs whether for warmth or cuteness, and that interaction and enjoyment can be a bonding experience between the dog and the owner. That being said some owners take it too far. When the dog is unable to move freely or is subjected to uncomfortable clothes like the tutu it is wrong in my opinion. I was at the emergency Vet and there was this small dog there that the owners had brought in because it fell and they wanted to make sure it was not hurt. The poor dog was wearing a t shirt that had big loops for the rear legs to go through that were loose and hung down touching it's feet. As the poor dog was walking around it kept lifting it's back feet and shaking them and sort of tripping over the loose loops. There was no way that dog could have walked or run normally with that t-shirt on. When I asked the owners if the dog fell because of tripping over the loops they looked at me like I was crazy. They really could not see how uncomfortable the dog was.
