Each ear is shaped different, so finding good waterproof headphones is a tricky task. You can’t just rely on other reviews, as you might have a totally different experience!
Common problems with waterproof headphones are that they don’t fit in your ear and just flood with water.
Another problem is that the sound quality is very bad because the decibel output is not high enough, that means the waterproof headphones are not powerful enough.
If the wiring on your waterproof headphones is bad, they will rust or damage easily. If you are skilled, you can re-solder, but the best is to just try to avoid it and buy descent waterproof headphones from the start.
Expensive headphones are definitely worth it. They seal off the water, feel pretty comfortable in the ear (or actually, the best is when you don’t feel them), and they have great sound. Audio should be good enough so you can listen to music and not just podcasts.
I’ve tried a lot of different waterproof headphones and the Wetplugs that come with the Wetplayer are by far the best.
(And btw, you can use them on any waterproof mp3 player or normal mp3 player with waterproof case — I have used them with a waterproofed Ipod Shuffle — really great solution that fits onto the back of your head)
There is definitely a little bit of a learning curve to get started with any waterproof headphones, but once you get a feel for putting them in right, they add about one minute to your pre-swim routine and are definitely worth it.
I swim continuously on my back, ears submerged. Sound is excellent. Plan to wash chlorine and salt out after each use by quick dip (of the phones, not me) in distilled H2O.
Earphones are personal, but these fit my small ears just fine, and the sound is great. (There are two sizes of rubber inserts included, and I’m using the smaller one but the larger one also fits me.)
What also helps is to make sure that they are firmly seated in the ear canal. I learned the “pull your ear flap back” trick long ago and it makes all the difference as it temporarily stretches the opening to your ear to make insertion easier. It sounds silly, but try it and see!