A little background: College student, been using very low-end ear buds for most of my life, and would like to purchase a nice pair of headphones. I listen to basically all genres, but most of my listening consists of all forms of rock, electronica, dub-step, trance, hip-hop, and rap. I will be using my iphone 4 and my laptop as my source of music, playing at around 75% - 85% volume for my ear buds, and I don't have an amp.
The specifics would be that they wont cause trouble while skateboarding, wont annoy anyone while studying at the library, and are comfy enough for those 8+ hour study sessions. I would prefer it if the cost would be a maximum of $100. I enjoy hearing the nice bass in the rock/electronic/hip hop songs, but being able to listen to some calming acoustic guitar is a must. I would appreciate something a little bit stylish looking to wear around campus, but it's not a necessity. Also, I'm on video chat quite often and would like to be able to use these comfortably on there as well.
Through some research, it originally came down to the Sennheiser HD555's and the HD280's, but both have their issues. I have read that the 555's leak a lot of sound, which would cause a problem while in the library, but they are incredibly comfortable. The 280's are a bit big, which might cause a problem while skateboarding, they clamp, which would be tough on the long study sessions, but they provide some great bass (even better when modded).
I'd be more than happy to provide any additional info and thank you for any help that you can give. So, any suggestions for a newbie in the community?