I find on-ears tiring after an hour or so of listening. I have a set of Denon over-the-ear noise canceling that I use for airplane travel and like. B&W just came out with an over-the-ear model (P7). I haven't listened to them yet but their on-ear phones sound pretty good (neither of those are Bluetooth). I find that headphone recommendations are very personal. You will find some people who absolutely hate any headphones designed by speaker companies while others are more open minded. I love the open-back Grado 'phones for general listening, but those wouldn't be suitable for a crowded train. For the budget you're talking, you should pretty much have any option you want open to you. Find a good local store and go listen. Guitar Center has a wide selection of cans, although I'm not sure about Bluetooth.