To me, it's more of the mentality of it all rather than the actual outfits that I find annoying. I just think it's so weird that skating is something that at one point in time was raw and street skating was the embodiment of the "don't give a fuck what people think" attitude. But, when you so deliberately spend time rolling up your pant cuffs just the perfect length so people can see just the perfect amount of sock, or follow and recreate what exactly is going on in men's fashion at the time, you're not doing these things for yourself. These are things you do in order for other people to see and create their opinions of you off that image thus negating any 'don't give a fuck what people think" aspect left in the skating . Not to mention that it seems like most people who go for this look might be trying to make up for something they are lacking in their skating (exceptions to this rule include but are not limited to: Dylan, Austyn and AO who all clearly rip). I'm just saying, let your skating do the talking, not your outfit. Westgate, GT, PJ and Leo are some of the most prolific skaters of this time and you won't catch them rockin' any urban outfitters hipster shit, because they let their skating make an impact in the skate world instead of their image. To me these outfits are nothing but what make up is to a girl, something to add flash and distract you.
But this is all just my opinion and I could be taking all of this shit way too seriously which I probably am for no apparent reason. Who knows. Just throwin in my 2 cents.