I tend to leave my headphones in my backpack or jacket pocket. (well, actually both, they are so cheap that I have a half dozen sets of earbuds scattered around different places - I have a nice ~$150 set of earbuds at my desk at work, and cheap < $20 sets everywhere else)

If I have to charge them then I have to remember to take them out and plug them in, and also then have to remember to take them out of the charger and take them with me.

I'm not super sensitive to sound quality, but charging is a deal breaker.