I’ve had bluetooth headphones multiple times before including in ear style ones with a stap between them, but the strap bothered me and they never quite fit right anyway (Backbeat Go2).
I’ve had over the head style although that was a long while ago now… pre iPhone 3G days, early 2000’s long ago… In those days bluetooth was still sort of new and shiny, so while they were OK, they had audio sync issues with video on Windows Mobile, probably more a technology of the day issue that anything much else. They also had a ridiculously bright blue LED that would flash constantly when in use which got REALLY annoying when you were sitting on a train in Winter (in the dark) with it reflecting off the glass every few seconds.
I’m sure the over the head ones are much much better these days, probably provide better sound than buds and isolate/insulate better (although I don’t know that I want them against my head in Australian summer during my commute).
The AirPods sit very nicely, sound pretty good (to me at least) and did I mention they are nice and freeing? It’s almost like they are not there.