I need your opinion (?)

What is up with this look ?

Well, It was Mr. Boyd's 50th birthday celebration. It's been going on for a month (that is a story for another day) I made reservations at Christopher's downtown in the Peery Hotel. I purchased him some new summer duds. (This is a man that NEVER, and I say NEVER purchases himself anything to wear. ) He would wear the same old thread-bare items forever. Plus, I must add, he will never forgo comfort for style, if it feels good (natural fibers are what he likes, he doesn't know this!) he always strokes whatever I purchase for him to wear, and he can tell if he likes the "feel" or not. Any-hoo, here he is in some new khaki shorts and a lovely Hawaiian print shirt and he looks smashing from the ankles up!!! But, he has on a skanky old pair of athletic shoes and some ankle socks. When I say, "You need to change your shoes" he informs me "like hell I do, these feel good, I'm wearin' em." So, he schleps into Christopher's with his "quirky" little "look". Bless his heart. . . . . . and all his other parts. I love him! Now for the 64-dollare question, is he a goof or what?