I only wear a bra when I have to. If I'm going out, sure. If I'm going to my friend's house, sometimes I won't bother. We're close and don't keep up pretense with each other so there's no judgment if I show up in jammies.
Jammies! I haven't had those since I was a kid, myself. However, I'll go out in thin athletic type wear which is ineffective at hiding the contours of my body. I have been the topic of a conversation nearby where the person was being just loud enough for me to be able to perceive when remarking something about people going out in their jammies. It just made me smile and chuckle to myself.
My wife is just a tad older and is also much younger looking; however, she is not confidant with her looks or body. I wish she would go braless; I love the look, but she says she doesn't boob that sag way down when she is older.
I also think that if your comfortable with your body and confident in yourself I think do what you want when you want and however you want because that is all that matters
My wife was really in her prime in her forties. Only bras she ever wore were sheer. Her nipples were always on display. Easily the most popular mom to the High school boys. Every guy would literally take a good look at her c cups and her perfectly erect nipples.
