Well, my $80 set is pretty unfashionable*. But it goes well with my overall very unfashionable wardrobe. And as with all audio stuff, there is a point of diminishing returns on audio (more money can yield incrementally better results, but is it worth it?)–but some people are willing to go further beyond that point than others. $300 for good headphones is still an excellent deal over an equivalent-sounding speaker setup, though.
* And it should be noted I’ve been called a cheapskate by quite a lot of people.