Sometime last year I contributed to a TES forum about headphones for ICT. Everyone seems to have the same problem - headphones in school get wrecked... and horribly quickly. If you are sufficiently anal you can hover over students while they connect and disconnect and make sure they have plastic bags to stop cable tangles. The more blokish tend to buy ultra-cheap headphones and replace them frequently.
Observation suggests the biggest problems are getting out and (worse) putting away. Children tend to remove the jack plugs by pulling the lead and in consequence the plugs come off. If you don't keep an eagle eye out, students dump headphones in a box and run for it - leaving the lead spaghetti for some other poor soul to sort out.
The picture illustrates my solution to these problems - hang the headphones on one side/ back of the monitor on a plastic self-adhesive hook (£1.00 for three). The jackplug is connected via the sound card at the back of the machine et voila the headphones are stored tidily and ready for use when needed.
These phones are a compromise - £5.00 a pair - decent rather than hifi. I avoid the headset variety with a built in microphone - they get wrecked even quicker than this type by students fiddling with the microphone while listening. We use separate desktop Logitech USB mikes when microphones are required.
The strip below can be printed as an A4 Poster from here