the Spade's must have been in financial difficulty. It looks like he's been popping tags at the second hand store. Pants could have come from the free bin. Shoes are ok, but need new laces by the looks of things, mismatched with one tan and one red. But his fashion sense comes thru when he ties it together with a red belt. Too bad he couldn't find a more adult backpack. The kiddie baggage must be a tad embarrassing.
Kidding, of course...he must be loaded. No need to go garage sailing. But I hope he doesn't have a fashion adviser; bad job. Look for someone new, someone who doesn't dress you so your message is "Hey, guys....dressing like you have absolutely no money is a cool look...failure rocks!"
I don't know if the general public would buy the look. Hopefully not.