Bedphones Gen 3.5
Bedphones are a pair of sleep headphones I've used to sleep with for over a year. These small, thin headphones don't quite disappear while laying my head on a pillow, but it is comfortable enough that I can fall asleep with them on.
The cord is long enough to keep a phone on the night stand and while I often wake up with them on the floor, I don't get tangled up and I have yet to pull my phone off the night stand.
If you've used an older model it is worth looking into the more durable new version that includes more comfortable ear wraps with a better fit to your head and a thicker cord.
If you want a wireless option, you can upgrade to the $99.95 Bedphones wireless sleep headphones that offer the same style, but with no cord to run back to your phone. This also allows you to avoid the headband style, which may be too warm for some users.
$59.95 at BedPhones