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I'm addicted
I had been in my stepmom's bathroom looking for tweezers and I had noticed she had a couple bras laying around there. So, as a bra enthusiast, I checked the tags. 38D. A freaking 38D. This woman is most likely a 34, maybe a 36 at most. I would then give her a cup size of a G-HH, or even higher. With the poor bras she's wearing, I wouldn't be able to guess properly. I think a good fitting bra would do her well, she'd look a lot slimmer and her clothes would flatter her a lot more.
How do I approach the subject? She had asked me so long ago about getting new bras but the measuring part had been too much for her and she just said screw it and she'll stick to her 38Ds. Just...ugh.
You might want to give her one of your bras to asses the fit. The band will probably be too snug so just hold it back with your hands, but the cups shouldn't be that far off, no? That's the easiest way to asses her size - look at the cup fit and then sistersize it up or down, depending on the fit. If you still have those freya bras, that could work cup wise, no?
Perhaps you could approach it from a medical angle. My mom just turned 70 and in the past few years has begun to suffer severe back pain (accompanied by obvious curvature) from osteoporosis. She's a tiny thing, but busty - probably a 30-32HH+. But she grew up in the deep South US with poor nutrition and even worse bra-ducation. I have no doubt that a properly fitting bra with decent support would have prevented a goodly portion of her problem. I wish I'd had my bra epiphany years ago so I could have helped her. You could order a couple bras for her from a returnable source online & tell her "because I said so" ;) You might be able to prevent her from serious misery down the road.