I think the capris are out--not because you're a pear, but because the length makes them unflattering, and they would be unflattering on most people I think. I think walk shorts or clams are pretty universally flattering. If clams are too skinny for your comfort, stick to walk shorts. This length is making you look a bit squatter than you really are.
As for the pencil skirt, I actually think it's not high enough and that's why you're getting the accentuation where you don't want it (though I don't think it looks nearly as bad as you think). Pencil skirts really have to hit at the natural waist, IMO. The A-line skirt seems a little long to me, but if it were shorter it might look too little-girlish. I think you would look great in a more structured A-line skirt or a high-waisted pencil skirt though.
It's kind of hard to see the eyelet jacket since it's black on black, but it seems like a keeper and you obviously love it.