My nipples are permanently erect as well, and I've had a lot of the same dilemmas, as you said, not because I have any real issue with them, but because of what that seems to convey to the world. When I went to a topless optional resort for vacation, I didn't wear a bra all week (even though many women did wear them when they were dressed, out of habit). It was just the best thing, and I didn't worry about what others thought because they'd seen my naked breasts all day by the pool, so what did it matter if my nipples showed in the evening? Heaven!