I'm sure you'll make this work. I am also short and short-waisted, and I've been playing with this look for awhile, trying to get it right for me. I find that a pant length like that in picture 1 is the generally most flattering for me. Going shorter seems to create the same problem as a too-short pencil skirt on petites: it ends up looking like a square. The slightly longer crops, especially if they create an A-line shape, avoid the blocky rectangular look. Shorter crops are airy and cool for hot weather, though, so I have a couple of those, too. Both lengths look terrific with the sort of boxy top you've pictured. These are actually great disguises for short waists, because they stand away from the body. It took me a ridiculously long time to figure out that--duh!--tops, even t-shirts, can be shortened. I now fold up the hems on all my tops to see whether hemming would make a difference, and it almost always does, whether a half-inch or 3 inches. Have you experimented with pinning up your long wide pants, to see how you like different lengths? Sometimes I pin and re-pin 3 or 4 times before I settle on the right length. Different pants--and tops--seem to require different lengths for the most flattering proportions on petites. I like the looks you've shown here, a lot.