Anne, first of all you are lovely. To me, you look svelte and strong in all these photos, and I absolutely love your hair.
I am sad to see you being so hard on yourself! I do it, too, but I honestly feel you are somehow only seeing tiny things that I don't think look bad at all. Some days our own eyes are kinder than others, so I hope yours will soon see the beautiful things that we all see in your pictures.
Would you mind sharing which pattern you used to make the shirt in #3? It's perfect on you.
I do agree that your two nipped in looks are very flattering. Great to discover something that works for you. About the dress, I love it on you. I don't think you look flat-chested at all, just slim and gorgeous. But, if it makes you feel less than fab, the heck with it. I've had things like that that everyone else loved on me that just never felt right and by the end of the day I am itching to take them off. If this dress is like that for you, say goodbye without regrets.
re: feeling flat-chested, I am wondering where this is coming from. It seems like you've got an idea in your head that your chest needs to be a certain size for you to feel good, which makes me wonder where that came from. Is this something from formative years, something caused by societal influence, what's going on here? Just my own thoughts, but it seems like if you could figure that out, it might help to work out a way of looking at yourself and seeing what we all see, which is a beautiful person with a perfectly proportioned chest.
Chests come in all shapes and sizes, and I have seen many, many, smaller chested women whose looks, figures, and clothes I was wildly envious of. Twiggy, for one, and you, for another (I remember seeing a picture of you in a red turtleneck that I just loved, but I cannot wear turtlenecks). While I have made peace with my own midsize chest, I do sometimes still wish I could pull off some of the fab smaller-chested looks. They're just not for me, but I love to see them on others.