It's quite difficult for women to tell. So many of us don't know how a bra that fits should look and feel like. Many think that if it makes your boobs look good and it feels comfortable, then it's a good fit, but it's not the case. So many things come into play. The gore (bit in the middle) should lie completely flat against your sternum. The cups shouldn't be gaping, wrinkling or overflowing. The straps shouldn't fall down or dig in. The most difficult thing to judge is whether the band fits or not, because you cannot judge this with your bra on properly. You have to put on the bra upsidedown, on the loosest clasp, with the cups facing down and not on your boobs, so you can judge the fit of the band independently. If you just wear your bra normally and your band feels super tight, this could actually be due to cups being too small - which is why you HAVE to test the band fit independently. It's so hard for women to know what a good fit should look and feel like, because a huge majority of lingerie brands put their models in ill-fitting bras.
It can be very difficult to tell, especially considering our breasts can be different sizes. A lot of women will go to lingerie stores and get fittings done which helps narrow down band and cup size, but it is not an easy process. I personally got a fitting done when I first started wearing padded bras, and I get them redone every few years if my bras don't fit as well. Our breasts also get bigger depending on our ovulation, any weight gain, pregnancy, etc, so I always get mine re-measured if necessary.
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