This is the Wooster/Peskowitz/blogger thing that I just don't get - no offense. Wooster takes it to an even further extreme with cargo pants and combat boots. What I can never quite grasp is at what venue/setting would a half "dressy" (i.e. db and tie) and half casual (tight cargo pants, colorful socks, double monks) outfit be suitable? I saw Wooster a few months back at Bruce Boyer's book signing at Leffot and its just as jarring visually in person.
But, then again, those guys are all fashion directors for stores like BG, Bloomingdales, Gilt, etc., so what do I know? Maybe you're just ahead of my curve, friend. . .