My dogs wear clothes every day unless we are actually going out and it's hot. Callie started wearing clothes as a puppy so she is used to them and if you hold the shirt or dress she will put her head and arms in herself. Joey has been wearing clothes since a puppy to but he would ocassionally take them off,he has thinner hair and gets cold very easy so he learned he needs them and he has started putting his own legs in. Penny is fine with clothes and has been getting very used to them. Yorkies don't have under coats just human like hair so they get colder easier. My office has a walk in closet and I hand their clothes on baby hangers. I dress them up for Halloween and other holidays. They aren't going to keep something on their head though because most dogs hate things on their heads. I only use collars for their rabies tag and Id tag and I buy yellow dog designs ones from
https://www.dogcollarsboutique.com. I am absolutely not a fan of martingale it is just like a choke collar and I would never use them on any dog. You risk trachea collapse by useing a collar or choke collar on any dog and the smaller they are the more likely it is to cause issues. Harnesses should be used when hooking them to the leash. Because they wear a collar all the time I try to go with soft comfortable collars.