Wife and I enjoy going to nude beaches, nude sauna centers and a nude swim on occasion, so she isn't shy at all.
Even when her sister, BIL or nephew join us.
But on those occasions, everybody is nude so she doesn't stand out.
However, she will rarely go out in public braless. For some reason she thinks she would draw too much attention and she claims her breasts are not as firm as they used to be after breastfeeding 2 kids (although I think she still looks gorgeous)
But at home or while on holiday (where nobody knows her) she does go braless more often. Usually wearing a tank top or a spaghetti straps top like in the pics below. Some of them not transparant, only showing her nipples pointing. Others are semi transparant, clearly showing her areolas and nipples when the sun/light shines the right way.
No need to tell you which ones I prefer

And not only me, but several people have seen her wearing the semi transparant ones, including some friends and my dad. Only when her stepdad or stepbrother are coming round, she will go change into a decent top, including bra.
Enjoy the pics!