I have younger sisters who are 4-year-old twins and they regularly dress up the younger dog, who they still call a baby puppy (he is not). He gets to wear some of everything: shirts, hats, necklaces, scarves. He doesn't tolerate it quite as well your dog it seems lol. My dog will pull it off, or run to a different room.
Buster puts himself in the middle of the girls' play regularly. If they're playing with stuffed toys, he brings his own. If they're playing dress up, he jumps right in and willingly wears anything that fits him. I think he likes to play dress up, he loves any attention (even though he gets tons more is always welcome) and having his picture taken.
He wears scarves too! I had just picked this scarf up off of the floor when Bus came running over with his neck held out as if saying "put it on me!!!"
None of this is done against his will, I am always close by when the girls are playing with Bus. While he's always been very gentle with them, the size difference is an accident waiting to happen. My littlest is barely 50lbs, Bus was 140lbs in Feb. (and likely still is).