It's hipster in like Macklmemore is hipster, wearing weird looking clothes in the idea of trying to be different to try create visual interest but its just not a good look. They just look sloppy IMO but are probably comfortable but if you want comfort just wear some Nike trainers or maybe some more simple Clark's there's plenty of colors of those dessert boots.
The inherent problem with this argument is that weird/ugly is entirely subjective. I agree that they're a bit...obtuse (not sure the word?) but they have a unique look that fits with my style.
Also, if you want to discount fashion that is predicated on deliberate ugliness things are going to get ugly fast. Would you consider The Soloist, CdG, or Rick Owens 'hipster'?
*edit* subjective not objective
Edited by TWorksheets - 7/9/13 at 4:25am