I admit I haven’t got much of a dog in the bra fight. Mine are more like puppies than full-grown hounds, and unless I test positive for BRCA and need them cut off and replaced, ain’t no way they’ll ever top a B.
In terms of unnatural restraints on my girls, I don’t, as a rule, go for anything too terribly unnatural. On Coobie days, they are perfectly happy to sit inside the molded cups, nipples only a little squashed. I don’t do EXTREME PUSH-UPS!!!! because my body hates that; you’ll never catch me in a bra that’s mostly full of foam, turning my low-lying boobs into babyheads (second definition, please). A little curvature out of a good supportive plunge bra? I’ll take it, but the shape has to look like it belongs on my body. I am a bottom-heavy hourglass: brilliant hip spring, subtle bust, nipped-in waist and proportional bones.
My breasts may want their freedom but they don’t exactly suffer in their bondage. I examine and wash them on the regular, which is plenty of massage. Milk production is out of the question, and they splay so wide that if I clutch anyone to my bosom, chances are she’s hitting my sternum.
Is it healthy to wear an uncomfortable, ill-fitting bra? Probably not. But it’s not healthy to wear other uncomfortable, ill-fitting clothes, either. I wouldn’t wear my jeans too tight. I wouldn’t let my shoes scrape the backs of my heels away — and that happens in flats, so no “spikes are evil!” lectures. The most supportive shoes I ever owned were a pair of vinyl platform boots with six-inch heels. I don’t let my bras dig in at the band; I extend them until the pressure is just firm enough. I don’t ask them to do the impossible. I happen to love my natural size, even if the shape and, er, position disappoint me some. That disappointment comes from my own aesthetic, formed from years of looking at women’s bodies in art and historical costume. It doesn’t come from Playboy (is that even a thing anymore?) or porn (all fake anyhow).
Whatever you decide on the matter, the key is that you made the decision. At the end of the day, they’re your breasts. I can give advice. I can tell you what works for me. I cannot tell you how you relate to your own body, or feel what you feel, physically or emotionally. I will love you with or without a bra because you deserve to be loved, full stop.