I was in college when the first iPod came out. As an early adopter that was super into my music that first year or so, wearing white headphones around campus actually came with more social interaction. It felt like everyone was staring at me and usually people constantly interrupted my jam sessions to ask me about them. The novelty quickly wore off for me, I realized I preferred a more private speakered environment for my jams. I also did and still suffer from massive pain caused from most in ear headphones, even the recent AirPods with adjustable silicone tips I use sparingly and never more than a hour or so.

What was weird was about 2 years later it completely flipped. I had written off my iPod in public while the entire world adopted them. I went from being the only one on a bus with white corded buds, usually recipient of people’s gazes, I was being antisocial and everyone’s eyes were telling about it. To suddenly, I was the only one engaged. Everyone else was being antisocial. This was well before the iPhone but people still just stared at their play list and stopped interacting. A quiet bus full of college students was a strange thing to witness but it took over as the social norm.

> I also did and still suffer from massive pain caused from most in ear headphones, even the recent AirPods with adjustable silicone tips I use sparingly and never more than a hour or so.

Have you tried replacing them with foam tips?