I put Copper in t-shirts and sweaters if it is cold. He does tend to get cold at times. I make his harness vests...so when we walk in the park or go in the car, I put him in a harness vest with a ring on the back. I don't attach the leash to his collar because of possible neck injury.
When I got him, I bought him at least 3 fairly pricy strap type harnesses. What a joke! They were mostly too big or appeared ill fitted or uncomfortable. The last time I tried one of these....I put it on him and made a quick run to the bathroom before our walk - when I came out, I discovered he had managed to wiggle around enough that the thing was now on upside down with the ring hanging from his tummy. I said, "Ok Houdini, we are done with this kind of harness." (I still can't figure out how he did that.)
The velcro harness vest is easy to put on and take off when our walk is done. I try to make them cute. I've had a couple of comments from people who think dogs in clothes are ridiculous, but I find them practical and don't care what others think. I'm not a person who would usually put clothes on a dog, but yorkies seem to have times that almost require them.