I really like the HD280s. I use them for school all the time. How would you say they compare to the Sonys? Whenever i'm in the car, there's music on, but i can't really listen to it actively. Same with when i'm walking around somewhere. I have travel headphones but i use them mostly on my hour long train rides to and from class. I tend to have a hard time listening to music passively. It either gets 100% of my focus or zero. I would like to at some point get a nice record player (and some records!) for those nights when i'm feeling romantic.
I prefer the HD280's but it could just be because they are new to me and bring a new perspective and frankly, they're more comfortable. I'm probably able to give music my full attention while driving, in the same way you are able to on the train. When I drive it tends to be easy-going freeway driving and not much thought is needed. That said, I'm also able to treat music like a soundtrack to my life. I LOVE doing that, like I said in airports or new cities, it's a blast. my favorite music listening experience ever was with a crappy pair of stock iPod earbuds.