I think sometimes you have to do things that you'd rather not do...and that's life. However, I have found that a bra helps define my breasts and sometimes makes them look even better under certain clothes. I have tried to not wear a bra and I don't like the way they look. Although if I never compared, bra/no bra, I wouldn't have known.
I don't know how you'd go around telling her, but you could say, you know I bet a bra could give some lift which could make you look even better than you already do in that dress. But don't treat her like a child with fake excitement and prance in with a bra and hand it to her like she's a puppy. I'm sure she's an intelligent woman and she'll do what she wants. Just be blunt and ask her questions. Meaning like, "Do you think a bra would make the dress look even better on you?" "Is there something else you can wear that doesn't need a bra?" etc.
Don't stress it, this is a small issue in life.
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