I personally find Sennheiser's higher-end (HD6x0/ HD800) to look rather nice. And why do the looks really matter if they're on your head and you're enjoying musical bliss? Besides, Sennheiser is German, so consider them to be like the Porsche of design. The HD6x0 would be the 911, which is classically designed and has stuck with a well recongnised and generally well-liked tradition. The HD800s would be the Carrera GT (or now the 918 Spyder), with the lower Sennheiser models being compared to the Boxster and Cayman. Just because they don't look as different as everything else doesn't mean that they are terrible to drive. Quite the opposite in fact.
Obviously this is a weird analogy, but I thought it made sense; so I apologise if it doesn't.
The analogy works perfectly, and I agree that Sennheiser makes awesome looking headphones. I want to say that the design isn't modern enough, but I'm not sure thats what it really is, they do have a very modern design. I guess it all comes down to 'bling' lol. When it comes to Grados (extreme example), many people will like the retro design, and a lot of younger people will just see it as 'old'.
When the average joe needs to buy a car, they get a low end or even used car. It's only the rich folk, or those who really want performance (and are willing to eat kraft dinner every night to afford it) go for the Porsche. You could say that the beats are like the 2010 Camaro, faster than the average Civic, but will get completely dusted by a Porsche.
Thank you, that's exactly what I was going for.