At home, I have 3 computers and an iPad that all feed into an audio mixer.
That mixer feeds a pair of Yamaha HS-5 desktop studio monitor speakers as well as a Behringer 5-output headphone amplifier.
During the day I listen on the Yamaha speakers, at night, with a light-weight pair of over-the-ear Sony headphones with 40mm drivers, and if I am writing, recording, tracking and mixing my own music, I will instead use my 30 yr old AKG K-240 studio headphones, which are circum-aural (they surround the entire ear) and have 65mm drivers.
The above listening also includes YouTube, music on my local PLEX media server, internet radio streams, and sometimes brown noise, or binaural beats if I am trying to work and need to focus and close off distractions. When working (software) I typically will wear the above mentioned Sony headphones.
On the go, I have 128kbps MP3s on my phone which I listen to with an ancient pair of Sony Walkman headphones. I squish them down compressed like this (with Selene Media Convertor on Linux) to save space and fit more music on the 32GB microSD card on my phone, and I'm
never going to lug around a set of proper cans, and only will be listening on lighter and smaller headphones (Apple Earbuds and similar do not fit my ears, and are either very uncomfortable for me, or slip out or
feel like they will slip out, so I do not use them). If you ever see me wearing BEATS headphones, please kick me in the head until I pass out and then steal them and run away, I will not mind
. They are an abomination to look at for me. Never, not for me.
In the car, I seldom listen to music any more, and either put on NPR, or just enjoy the silence. There's too much to fiddle with between the smarphone answering calls (I don not initiate calls while in motion), GPS Nav, and adding the head-space to fiddle with music is just too distracting to me. I like to actually pay attention to the road and not crash or die since most other drivers are completely reckless or distracted so I need to stay vigilant.