Bertie can be quite emotionally clumsy with nearly everyone else, but he does understand Jeeves. :)
Gosh. I speak as someone who likes suits, and who feels suits ought to look like suits. That suit sounds horrifying! If even Bertie felt a touch off seeing it, I'm not sure how Jeeves didn't fall in a dead faint at the door! I hate sports-themed garments. I'd cry at the sight of that underwear, too.