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I use most of them, so in this order:

Earphones
Headphones
Stero System

I have a stereo in my room, and I have a set of portable speakers which I never use because they're fairly bad quality.

In my room = Boombox.

Everywhere else = headphones.

Speakers, unless I'm driving, then I use the car's stereo

By "headphones", do you mean "headset"?
And by "earphones", do you mean "earbuds"?
Because in that case, neither.
I listen to most of the music I listen to through my car stereo.

Picture Time!

In the house I use this connected to some of these.

On the move, I use a pair of these.

In the car, I use the car's built in soundsystem, which is alright...

yaaaaaaAAAAAAAAaaaaaaaAAAAAAAAaaaaaaaaaaAAAAAAAAaaaaaaay
\o/

Oh man, Rotel is beastly. You guys are going to laugh at my outdated computer speakers. I have 4 sets.

Various things at various times—earphones with my MP3 player when I'm out or in bed, headphones when I'm at home at night, and PC speakers at all other times. PC speakers would be the most used of those three, but I'm not sure what category they fall under—'casual speakers'? I have no idea what that might be, but that might be it.

I usually use my Skullcandy TiTANs, but when I'm at my friend's house, I either use my laptop speakers or his Logitech Z5500.

My uncle got me some high-end in-ear headphones a year ago, and they're fantastic; I use them primarily on my iPod. Usually, though, I'm on my computer, using a less luxurious though still very well-made headset. The bass on these is astounding, as is the overall sound quality.

A few years ago, when I was staying with my brother for some holiday break at MIT, we dragged in these obnoxiously huge bass speakers that a friend of his had sitting around. They were maybe 1.5 meters tall, and we had to work together to move them to the corners of the room. Then we proceeded to watch the DVD with these enormous speakers... on a 15.4" laptop screen.
I couldn't tell the difference in the sound quality between those massive speakers and the simple pair I use at home, so I've never seen the point in buying expensive sound equipment.

I can't stand earbuds/headphones... I just have to have music around in the air, or something.

Mostly, I listen on this beautiful pair of Bose computer speakers I got for Christmas a few years back. They sound amazing and crisp and clear and they're my babies and I absolutely love them.

Headphones. Bass for the win.

I absolutely hate earphones. therefore, headphones.

All. But by choice: my awesome speakers and subwoofer, headphones, earphones, anything else.