I'm 28 years old and I too at times have thought about wearing in the future. I don't dwell on it much though because I think it's more important to focus on the now rather than what may or may not be ahead.

With that said though, I always figured I would stop wearing altogether at some point when I'm much older. No specific time/age, just some point where I say screw it and stop wearing. For me at least, half my friends and family know I wear. I told them at some point and all of them have been cool with it. In fact, they have been so accustomed with me wearing, they (as well as I) have forgotten that I wear in the first place. So if that day ever comes when I decide not to wear anymore, it'll be a surprise to hardly anyone (anyone that matters anyway).

But as I said earlier, I don't worry about that too much. I'm happy wearing now and that is what's important. Those are future concerns. I'll let future me worry about that!