I HATE SPENDING TONS OF MONEY ON BRAS! I'm in a similar situation, my weights been going up and down and so is my cup size. And now I have to reinvest in a bra collection because I DARED to gain/lose 10lbs? -__- Not ok body. Not. Ok.
Check out NYX's reds. I have a matte red from them and it's one of the best I've ever tried. Super pigmented, not too drying (all matte lipsticks are dry to me. That's the nature of the beast), and if you can find them on the ground not to expensive either.