Best answer: Most bone conduction headphones are designed to be comfortable even when working out, so you can enjoy them for as long as you want.
Amazon: AfterShokz Trekz Titanium ($100)
Designed to disappear on your head
Bone conduction headphones are a little different from your average set of headphones. Instead of covering your ears with little speakers or tiny drivers you shove into your ears to drown out the world, these headphones rest near the ear and vibrate sound into your body. The vibrations travel through a special bone near your ear called the Mastoid Process, and the end result is you can hear both the sound from your headphones and the sounds in the rest of the world as though they're coming from the same places.
These headphones are easy to wear all day without issue.
But what does that mean for comfort? These headphones need to be touching the sides of your head in order to work, and it needs to press with a little bit of pressure for the best experience. When you put these headphones on, they feel a little snug. But they're also designed to be worn in almost every environment, so the material pressing against your head is similar to the softer sporty material you'd see on a fitness tracker you wear on your wrist. These headphones are designed to be worn as you work out, in particular outside. I wear mine for long distance cycling, specifically because it's lightweight and comfortable and you can hear everything around you.
Perhaps most interesting about these headphones is how quickly you can forget you are wearing them. That pressure on either side of your head is fairly easy to adjust to, and once you do these headphones are easy to wear all day without issue. On multiple occasions I have walked in to a meeting and caught a funny look from someone wondering what I was wearing, because I'd forgotten to remove my bone conduction headphones. It's easy to forget them if you can't feel them!
The one thing I can't do with most bone conduction headphones is lay down with them on. The design is often fairly rigid, and that includes the band that runs across the back of my neck. If I try to lay down on these headphones, the rigid band pushes back and either becomes uncomfortable or moves the headphones away from the place I need them to be in order to hear anything. In any other situation, however, I find these headphones incredibly comfortable.
Fully active headphones, for fully active people.
Some of the best headphones for people who want to listen to music while working out or walking around a busy city. Easily the best bone conduction headphones you can buy.
