i heard sleeping with a bra is bad for your health. :/
as for going out, i sometimes go braless if i'm wearing one of those tight stretchy tops that restricts boob mvmt and/or a thick (buttoned-up)jacket on top. i cringe when i see people with nipples poking through their shirts in public.
Nipples poking through the shirt is a huge fear of mine, idk how much other people actually care about it but I was teased pretty brutally about it some time ago and it's made me really self conscious about my chest in clothing.
My breasts aren't big, but they're not that small, especially in proportion to me as a whole so I'd feel uncomfortable doing that I think, kind of exposed and they'd jiggle around and stuff if I was running. But I don't sleep with a bra and sometimes don't wear one at home.
Only if I'm at home, a hotel room, or if I'm going to the bank to deposit money or if I go to the drive thru at any food place then no, I don't wear a bra. Other than that, I always make sure to wear one.
I wonder if the bra never was invented what women would wear then. And would there be more boob surgery? I mean the bra isn't a worldwide thing, in most countries (poor and hot climate) they never wear them.