Today's perception of what is hip is so extremely meta. Modern street-style appears to be based on a parody of itself, it is a whole culture of irony to the point of excess- if it had a flavour it would taste like a horseradish sandwich on mouldy bread. Style is so anti-cool that if you are dressed like your grandfather you're doing something right (not your grandmother though, she's too cool).
The latest Urban Outfitters, American Apparel etc branding seems to be built on a oneupsmanship of creating and matching traditionally ugly pieces and marketing them as uber hip. A little like recycling except more expensive than reused, dead trends should ever cost. The rule must be something like however much it cost when it was first popular multiplied by how many years between then and now.
It turns out that you can get away with wearing anything as long as you're doing it ironically. UO released a yellow T-shirt with the Star of David on the breast pocket because I guess they exhausted things that were ever considered cool to bring back so they moved on to things that were never cool like WW2. For the record, apparently it was just an ambiguous star and no one can be blamed for UO's Nazi throwbacks. So when they come out with white pointed hoodies, don't worry guys its just ironic.
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