It is 100% situational. I spend a lot of time in the car and therefore listen to a lot of music while driving. The stereo in my car isn't that bad, but it's not great either. I also listen to music with crappy ear buds on my phone often. This could be while running, or just walking around town. One of my favorite things to do is to walk around an unfamiliar city while listening to music. Another favorite thing to do is to walk around airports while listening to music. When I'm really lucky, I'll use my headphones, my nicer (nothing too fancy) headphones at home while listening to vinyl. Lately been using the Sennheisers but I also have those Sony's and some Audio Technica's. 
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.