I wonder if the headphones I use would work for you on your rides? They fit close and work by bone conduction instead of going on or in your ears, which works really well. Check out the Aftershokz, they have both wired and wireless. amazon link
I have a set of Aftershokz and I love them. I probably have a dozen sets of headphones/earbuds etc. and these are one of my favorites. They aren't quite up to the level of some of my Senn's but I never expected that. However, they do have incredible sound and (unless I have them cranked) I can still hear what is going on around me. Add a set of earplugs, when you don't need to hear the rest of the world, and you will be stunned.