Cheap or Chic?

There are a few things we could discuss here... but lets start with the shorts. On a recent trip to Brick Lane I noticed an astonishing amount of guys in cut off jean shorts. Literally every other person had them on (the rest had on skinny jeans, like spray-painted on skinny). I was pretty surprised to see this, because up until then I hadn't noticed any boys wearing do-it-yourself cut off jean shorts, and all of a sudden it was the biggest micro-trend around.
For those of you lucky enough to know me, you may have noticed that I've been living in my 10 quid Uncle Sam's levi cut off do-it-yourself-with-the-help-of-the-tailor (shh... i'm really not of the crafty variety) jeans all summer. I love them. They were cheap, no doubt. But all the reason to be even more fabulous. I sussed them out my self, only paid a tenner, and deliberately wore them day in day out despite being told repeatedly by a certain someone that I never would.
Honestly, I am not sure how flattering they really are. They can produce a slight wedgie effect, and I can say this truthfully only because I have witnessed quite a few other girls about with a similar situation going on with their similar shorts. It's true - old school levis have a tendency to creep up the old backside... but wasn't that in back then? I seem to recall photos of Cindy Crawford with that similar high waisted slight wedgie look from back in the day....
Anyway. Enough about that. The question is: cheap or chic?
Do we like these do it your self denim shorts? Will they last more than Summer 2009? Are they okay on guys? Are they really even okay on girls?
P.S. Boating hats? Really. I have seen two people attempt to pull them off this summer. This guy actually did it better than the first I saw. Hopefully we have seen the last of this, in my opinion.