Let me say I ALWAYS wear my helmet and nearly always listen to music when I ride. For those people who think they need to hear what is going on, if you rely on your hearing to alert you of danger you are going to die completely uniformed of it. Most vehicles are nearly silent these days so forget about hearing a problem before you see it.
I use a pair of Sennheiser CX-300s for a couple reasons when I ride. 
1. They are in ear buds that stay in without fatigueing my ears.
2. They were relatively inexpensive.
3. The sound quality is great for their price point.
4. The buds are small so they don’t hurt my ears when I am removing me helmet.
5. The in ear design blocks wind noise which makes listening completely possible.
There are plenty more options. I have not used these ear buds but I have recieved these on recomendations from other riders.
- Chatterbox. Supposedly you can plug your iPod into it and stream it through.
- V-Moda. More expensive than the CX-300s but greater bass response. Probably slightly large frames as well though.
- Shure and Ultimate Ears both make expensive high quality ear buds for the more obsessive listener. You have to be careful that you don’t buy a triple fi model because those get ridiculously large. They sound awesome though. Just get a smaller, cheaper pair. I love mine.
- Of course you can always go to your department store and buy some of the cheap in ear buds they have for $20. Those will absolutely work, just not with as much quality.
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I just like to say it how I see it. Take care.
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