Headphones and music

I have never listened to music while riding, my headphones would fall right out. I tried a pair of Bluetooth headphones a while ago but they didn't really fit. For me its not a priority, I would rather spend money on my bike.

I have both the Jaybirds and JBL Headset, the second one is in the "let in more outside noise" style of headphone. For biking though? The Jaybirds are **far** better.

Never drive and listen to the music - well, sometimes I sing (don't know if that counts)

not recommended to ride with headphones on

Certainly a bad idea I guess.

I'm a music lover; in fact, I hold a bachelor's degree in it. Out on the trail, however? I prefer to hear the sounds of nature. It actually bothers me a little to hear some dude rocking a bluetooth speaker in his backpack or something, even if I like the song and only hear it for a little while.
I'd never tell someone to shut down their tunes, but it does seem a little weird and disrespectful to me. So in that case, I'd say - definitely go with the headphones if you have to hear music. I'd warn against it for safety reasons, however.

OK is see OP was when Obama was Pres and the world made at least some sense. Anyways! I ride with headphones when I'm training on my road bike. It definitely helps disguise the pain a bit. Sometimes it's nice to have that, sometimes not. Same thing when running. Mountain biking is a different deal for me, so I would never ride with music but in any case, I think it's perfectly safe to ride with earbuds IF you can still hear your environment. That may sound like a paradox but I use Plantronics FIT. A bluetooth set that is designed to let like pretty much ALL of your environment in. It feels very safe and as long as the volume isn't maxed out, it kind of does feel like a soundtrack happening to your life (lol) versus being inside the music. They also sound super good imo with really good spacial sound stage. Very much not bass heavy though (which I also prefer).