Angie, I think the blue top is simultaneously too wide through the shoulder and too small in the arm, making it uncomfortable to reach forward in it. It's not a fit problem I've had before, so I'm kind of guessing what the problem is, but that's what it feels like.
Dresses are a no-go, as are skirts. I have some, and they don't get worn. They hang in my closet looking pretty and I love looking at them, which is why I still have them, but I don't wear them! The only exception would be something like the Free People tunic dress below, which I would wear over skinny jeans or maybe black ankle pants, if it came in my size, which it doesn't. (Sad! I love it.)
Firecracker, I *love* off-the-shoulder tops, and they are absolutely the most feminine thing I love (aside from glittery sandals, maybe). but I don't have a bra that works with them. I wear a 34K (UK sizing) bra, and so strapless is a challenge. For Halloween I have rigged up systems to cope...maybe I'll try an off-the-shoulder top and see if I can make it work. It'd be a fun change, anyway!
Below, I've added the gray pants I have (see, nice, but boring), and a couple items I've been considering...any thoughts? The Lucky top might be too casual for nicer nights out (like the ballet) but not for, say, the weird local modern dance performance I'm going to tomorrow!