I’ve had several earphone pair’s over the years. While not super expensive, some considerably more pricey than the ones typically included with phones. At first I just plugged them in, and put my phone on my pocket, and went with it. This caused a lot of strain on the jack. I cannot remember how long it took before I was left with only once of two channels working (only audio on one side). I could “fix” it, if I held the cable in a specific position.
Later I went on to buying cheaper ones, but still with the isolating silicon. Got a 3-pack. Having music is really important to me. Not necessarily as a “I don’t want to talk to anyone” thing, but more as a thing that just makes me happy.
Later on I got a maybe $45 SoundMAGIC earphones. Being very careful, it has lasted a while now (6+ months).
However, I recently got a ridiculously simple idea. Using a $1-ish 3.5 jack extender (10cm), that will be what breaks when the time comes. They are cheap, and small. You can easily carry a backup. It’s also small enough to fit in most containers.