High-fiving Angie, my dress twin! She's slimmer and a couple of inches taller than I am but the basic shape is similar (smack dab between a rectangle and slim hourglass) and I look best in the kinds of dresses that flatter her most: high necked sheaths. I like fit and flare, too, but have more luck with skirts paired with blouses or tops in this silhouette than in actual fit-and-flare dresses, probably because I am short waisted but not truly petite (so petite dresses are generally too short for me even though the waist placement is better).
I have a relatively strong shoulder line (my shoulders are the widest part of me in fact) so I can wear a shift pretty well, too, if it's cut right. And I like the look of that in summer, especially.
I can't fill out the top of a wrap dress, alas. I look even worse (if possible) in a "surplice" dress -- i.e. a faux wrap. Ugh.
Skirts should be either quite full or quite narrow (even tapered, esp. if midi length). The A lines that used to look so fab on me when I was just a bit curvier now hang sadly limp and foolish.
This is why I haven't found a shirt dress that I like. Many are A-line. The top portion would look fab on me (esp. if in a classic shirt-collar style) but an A line bottom would be less than fab.