I get your stance but I guess I'd say given the target (famous mainstream-ish rapper), any action/statement/etc done by ASAP would obviously be calculated as opposed to done organically. This isn't some homespun underground punk band, it's a rapper pushing the popular sound and clothing styles of the times. Some tactics may be unsavory, but trying to align yourself with the right brands/people is tough work, even for someone who has "made it".
Anyway, fashion/dressing "well" for a lot of guys is a pretty calculated thing to begin with. Very few on here threw together an outfit with ballin' clothing organically. I mean, unless you're terribly wealthy and stylish.