idk, I bought my portable system with looks partly in mind, ended up with an NWZ-A829 and AH-C751k's, they match, look very sleek, but also bring a lot of quality to the table (better than some fullsized 'phones can do)
its that they think they don't care, is what I'd have to say, I recently gave a pair of SR-60's to a good friend who was convinced my high end audio hobby was just a big cash sink, well that tune has since changed to "these are AMAZING, I didn't know you could actually hear all of these instruments at once and still pick them apart"
our eyes and ears will always prefer something more becoming, however our tastes are generally driven by our peers, which aren't always thinking with our interests in mind, hence brands like skullcandy being absorbed into chic culture
@ shmoreblore, can I ask who those people are, beyond knowing that one of them was in the news a whileback for some pornographic images or something, and the other one is a singer (I think? if not a guitarist or something?)