IMHO, ANY braless situation is a win for all.
Have posted previously have been trying to get my wife to go without more often. She is a fairly firm 34B and can easily do that with most tops, but her nips are frequently firm to rock hard and will show, a thing she is quite self conscious of and has taken to wearing padded bras to hide that fact. Over the past few years, with much encouragement, she has gone without, mostly on vacations but increasingly other times. I have implemented a "rule" [all in fun, not a D/s sort of thing] that she cannot wear a bra when returning from a business trip. Recently she was travelling for a few days and I sent her a reminder note about "the Rule." To my surprise, when I spoke with her on the morning of her return flight, she said she had already prepared to comply with the rule in the selection of her clothing. All good. When she arrived home, she was wearing a polo shirt, and a mid-thigh length skirt, pretty short for her at work. It was pretty obvious she was not wearing a bra as her nips were making distinctive points and in the right light her areola were visible. She said she changed at her hotel mid afternoon, had met a couple business associates while still at the hotel [which she said was embarassing but I think she really liked the feeling] and then travelled home. A pic of how the top looked is attached. Pretty good overall progress, which hopefully will continue.