Death Cab Decision

Despite the fact that I bought PLANS at Target, Death Cab is still cool. Had I bought a pair of Chuck Taylors at Target would they be any less cool? And are they any less cool because the unwashed masses have accepted them? I know these aen't universal rules, but ona case-by-case basis they apply. U2 and Radiohead are still realtively cool. And before anyone says anything, I understand that it is very hard for a 30+ year-old man to pull off Converse hightops. I may still be able to do Jack Purcells.