For the life of me, I cannot get in-ear headphones to stay in my ears. I don’t know if I’m uncoordinated, uninitiated, or aurally under-endowed. They are uncomfortable to put in and will usually fall out, as I’m usually working outside, moving around, walking, etc. Maybe exercising. Maybe.
I did get some hearing protectors with an MP3 jack to plug my player into. That works well for the nine months of the year that I’m blowing snow in Wisconsin, but not always the best solution.
I ended up using an older pair of small headphones, took off the fabric on the earbud, and after putting them in my ear put a silicone swimmer’s earplug over them. Looks funny but works great. They don’t fall out and have the added benefit of blocking outside noise, almost better than the ear protectors, so I don’t have to have them as loud. The seem to be more comfortable to sleep with as well.