I listen to music pretty much constantly, and it’s not unusual to see me on the road with just a carry-on and still have 3 or 4 headphones on me that I’m testing.
First off, Bluetooth changes everything. It’s so nice to not ever worry about cables, or even proximity for the most part, like having your phone charging by the laptop and still able to walk around the room. Audio quality is great now, only downside is having to charge something, but they’re all pretty good about battery now.
I’ve been enjoying a category I’ll call: Bluetooth, over ear headphones that let people know not to bother you, that you feel kind of cool wearing, that are great for planes, and cost around $300-400. The pioneer in this category is Beats, and I bought a pair of their Studio Wireless (in matte titanium, natch) after Apple bought them because I wanted to see what the fuss is about. More recently I got some horribly named but well-reviewed Samsung Level Overs, so this is a comparison of those two. (Another contender in this category would be the Parrot Zik ones, but just skip those. Great idea, annoying in practice.)
Main downsides: the cable it comes with doesn’t “work” with an iPhone or Mac as a mic or control device, and is also clunky. (Bluetooth control works fine.) This is apparently because the remote control resistor on Apple-targeted cables work differently from everyone else’s, which I think we can all agree in 2014 is ridiculous for both sides. My fix for this was to use the cable from the Beats, which you can also buy online, which looks cooler, is smaller, and works great with my Mac for G+ Hangouts and Skype calls. Perhaps related to this is when the Beats or many other Bluetooth headsets I’ve used are connected to the iPhone there’s a battery indicator and the Samsung doesn’t support this, but since the battery life is so good I don’t worry about this too much.
Extra credit: What headphones do I use in other categories? (An update to my 2009 post.) For in-ear wired I use Ultimate Ears 18 Pro Custom molded to my ears, but I also recommend Sennheiser IE 8i for friends who don’t want to go to audiologist, for running/exercise or when being discreet like on a subway I use the Plantronics BackBeat GO 2 with charging case, at home I like the Auduze LCD3 usually with a Red Wine Audio amp. I agree with many of the assessments in Marco Arment’s mega-review, and I got turned on to the Samsung’s by Wirecutter’s noise cancelling review.