Anonymous wrote:10:11/10:18 here: you should wear the J Crew shirt dancing - it seems like it would be nice and breezy so you wouldn't get too warm.

did you get it in black, or another color?
I have a friend who is in the same boat as you, except that she found out she was a size H! No sh*t. She may end up having a reduction at some point, due to frequent back pain. She ended up spending a fair amount of money on really good bras from a specialty lingerie store. (the one she likes is in Chicago.) They keep her measurements on file and she re-orders periodically. I'm a size A (after wearing B for years, then losing weight in the chest, argh), so I have the opposite problem as you. But like you, I have a hard time finding tops that look good. Some things flatten me out way too much and it seems like everybody is either naturally busty or has fake boobs these days, so a lot of shirts are made for that. I have to be really vigilant about bending over when I try stuff on - a lot of it totally gapes and then "free bra show!" Not a good thing.
My chestier friends tell me that button-down shirts are pretty much impossible - they either swim on you or gape. Button-downs are still tailored with guys in mind, I suspect. If you find a good button-down shirt that you like, buy several and take them to a tailor and see if they can be taken in so you're not tucking in as much material. (When you do tuck in shirts, start from the side seams and gather the material there so it doesn't create a front or back bulge under your pants/skirt. A photographer friend taught me that.) For winter, I would think that thick, stretchy knits are your friend - they'd cover the bust without straining, but also hug fairly close to the stomach so people could see you weren't heavy. v-necks are probably your best bet there, I would think. (oddly, they're flattering for the A-cup girls as well, go figure.)
The maternity-looking shirt has been in for a couple of years now, maybe because women are getting heavier and that's more flattering to the muffin-topped individual. It drove me crazy this past spring - I was done being pregnant and I'd gotten my body back, but all the stores were selling stuff that made me look pregnant again.
good luck on the date!