My old pair of wireless headphones gave up the ghost a while back. They'd lasted a couple of years, not a great lifetime, but I got good use while they lasted. Time for a new pair.
For a long time, I used wired headphones because wireless was just too unreliable. Static, disconnections, etc happened all the time, particularly while running outside. But things have changed in the last 4-5 years, and just about any Bluetooth headset these days provides pretty decent sound. Every once in a while you still run into an area where some kind of interference will cause static or stuttering, but it's rare. And it's so much more convenient not to have to worry about the wire getting caught on something, or reaching far enough to plug into your phone.
After some poking around the internet for reviews, I settled on the Plantronics Backbeat Fit. They're not cheap at a suggested price of $129.99, but Amazon had them for about 2/3 of that price. I got everything I was looking for: wireless, over-the-ear stability, and even a phone holder armband to use when jogging. The sound quality is great, and the battery will last several hours on a full charge.
So I'm all set with the new equipment, which will see heavy use while I'm out jogging around this summer. I'm happy with the performance, and time will tell if they're sturdy enough to last more than a couple of years.