Living in downtown Austin and observing the patrons of the numerous bars here, I've come to the conclusion that fashion is easy for males.
In any fashion era, the males who go to the trendy bars tend to wear the same outfits. Sometimes, it's almost as if there is a "uniform" that they wear, with perhaps some variations on it. You can usually go to Gap or Express and find the uniform. I think the uniformity of it is silly, but I've come to accept it.
For females, it doesn't seem as simple. There doesn't seem to be a "uniform"; originality consistently seems to be a bit more trendy than a single style.