Hi all, long time no post. I just HAD to pop back in and post this though, it may be of some use to someone.
I recently started physical therapy in the pool, and I wanted some music. I bought the waterproof Otterbox for my iPod mini, but i was stuck for headphones. As anyone who has searched knows, you can get mono diver's phones or you can get the worst quality earbuds on the face of the earth. Those are your choices.
Sure, there's the new case from H2O Audio, but you have to put up with a leaky case. The otterbox is 100% watertight, I've tested it extensively. But I digress.
I have a pair of Shure E2s sitting around as backups. I looked more closely and they appeared watertight except for the obvious port for the sound. I grabbed a pair of triple flange sleeves and after some cajoling, convinced the sleeves to cooperate and get on the E2s. I took the whole rig into the shower. It worked great! Obviously you have to make sure they stay in your ear and that they are tightly sealed, but since they sound awful unless they are sealed in yoru ear canal...that really isn't a problem. They work in the pool as well, even when I submerge my head a couple of times (just for a second or two each time).
So, a decent, fairly inexpensive pair of watertight earbuds has been with us all along. I do not recommend this for anything that costs more than the E2s on the off chance that I am wrong. I refuse to accept responsibility for your 500 or 1000 dollar buds if you take them in the water!