Start them young with anything you want to do with them.
Being cold here,we put a coat on the wife's dog. She is out for hours with me,but it's her dog.
She picks her legs up so we can put her feet though the holes of the coat. Well I really should say,so she can. The dog does it really all by herself. Comes off just as quick.
Another thing,I work at a hardware store,every 4th Saturday of the month the local animal shelter comes in and does nail trimming. We get many dogs in there that have never had that done. I feel so sorry for the dogs,they are so afraid. They can not understand what is happening to them.