Hey r/music, are there any high quality headphones that also look fancy?

I've been trying to convince a friend of mine to get the Sennheiser HD 555 or 595s since their last pair broke (some Sony model, but they've had Skullcandies before... Hnngh).

They're willing to spend up to $300, but I don't want them to waste their money on shoddy hardware that only looks pretty.

Also, what are your thoughts on earbuds? I know they're not good for ear-health, but they'd prefer something a bit more discreet than huge cans when they're out in public.

Thoughts?