Mr. B is an old soul and he believes a gentleman should follow certain rules. One of his steadfast rules is to don a hat when outdoors and doff a hat when indoors. Though not true gentlemen attire, Mr. B's chapeau of choice is a cap showing his Chicago pride.
Though in the summer, he gets dressed up a bit and dons his cowboy hats and fedoras
and in the winter he wears more functional caps that keep his head and ears warm.
He even have hats to compliment special occasions.
Like a true gentleman, if he forgets his hat, he makes do with whatever he has in paw or mouth.