Once it becomes widely adopted I doubt this will be much of a social issue. The value they provide is real. It's not some gimmicky thing. Tangled wires are extremely annoying and happens nearly every day I use them. Plus the wire gets in the way going jogging or caught on something with normal usage, etc etc. Lots of benefits to having wireless headphones.
Talking to yourself with a non obvious headset will always be awkward looking though.
The social issue thing is real and it's an interesting quandary.
I think my personal beef with them is when I interact with someone wearing an earpiece, it makes me think (rightly or wrongly) that they are happy to interact with me BUT at any moment a ping from their earpiece will be by default more important.
Maybe it's (perhaps in part) my own issue though.
On the other hand I can see the value in it, especially if Siri's abilities improve, and if speech recognition improves also.
Maybe I'm just old fashioned and in time this will built into our social fabric (I think back to the late 1980s and early 1990s when walking around with a handheld cell phone seemed incredibly dickish)
I never have the tangled wire issue.
1. You can either wrap it around in the box it came in
or
2. wound it in a circle and it stays as is.(That is how I put in in my laptop bag)
Talking to yourself with a non obvious headset will always be awkward looking though.