If I could, I'd go braless almost all the time - sometimes I really do enjoy the shape bras give me. Alas, the breasts are bigger now, so I can rarely get away with bralessness - and really, I never could because my nipples are more than a little noticeable.
I do go braless in our apartment building hallway, though. If I need to take stuff down to the trash room, I just wear a tee and cardigan, or a heavy shirt, so I'm at least a little more covered. When our dog was still alive, I did this, very occasionally, when taking her out to pee.
I just got back from vacation, where I stayed first at a friend's house, then with family. I planned my wardrobe so I wouldn't have to wear a bra with my lounge wear. At my friend's house, that meant just wearing whatever I wanted, because neither she nor her fiance cared if I was "properly" dressed. With family, it meant packing a cardigan so I'd have a second layer to pull over my tee.