You need a Good Dog hat with elastic or other earloops and a velcro or ribbon tie under the chin. like one of these www.BadDogHats.com

It may be best to start while they are young, but there is no reason you cant teach your old dog new tricks, its just knowing how to get him to wear that cute cowboy hat or jaunty beret!.

While showing your dog that you have treats in your hand, put the hat on pulling the ears through the loops. Then tie the under the chin strap. Hopefully he will be focused on getting the treat in your hand and not worrying about what you are doing to his ears. Often it is easier to measure roughly and remove the hat and tie the tie to the correct length while off his head, he may not be so patient while you are tying. Then pull the hat with the tied chinstrap on his head pulling his ears through. Tada!

Stop here and have him sit and focus while you finish adjusting the hat. When he tries to shake make a short sharp but loud sound like "hey" or a "Ak!"  this will distract him. When he is still and you have his attention, make sure you praise him and give him treats when he is doing it right.

At this point it is a good distraction to go for a walk, get the leash and head for the door, and he wont be worrying about what is on his head.

Once he is outside, he may shake but you can re-adjust the hat show him you still have treats and start walking. When he starts getting attention by wearing the hat he will become less opposed to the idea, especially when there are treats and walks involved!

Be prepared for a cuteness overload!

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