Thank you ALL for the lovely comments, I will try to get myself to wear more outfits like #2
Lynne - The stripey top in #1 is actually more fitted than comes across in the photos. I think overall proportions look off because I usually aim to shorten my torso a bit (like in #2 and #3) and this outfit makes my top and bottom more even in length; this is closer to my real proportions, but I don't usually style myself that way
Laura - The kitten heels in #1 are from last fall, and I couldn't find them online anywhere. The gray heels in #3 are recent though, from Target (these here). They are lightly cushioned and quite comfortable for their height. I highly recommend them if you can wear heels this tall, and like round toe shoes (I usually don't, but I do like this particular pair).
Ornela - The belt is just one with several mini-belts built in I was actually pretty surprised how well #2 came together myself! I think it is a good example of having the perfect pieces for the look, as well as for trying on combinations you think may not work: I almost didn't wear this shirt because I thought it wouldn't "go" but after I tried it on it was clear that it did. Same with the shoes, which worked once I'd selected this belt. And same with the hair, which I always do 2nd to last, and I would've worn a normal ponytail if I hadn't already picked the belt and shoes. Now that I write all that, it may also be tribute to the order in which I get dressed