Rachylou, I'm laughing at your comment about reading Kibbe. It's on my mind a lot lately, too, after recent posts here.
AM, you have described my style better than I could have. Your assessments of the outfits are enlightening. On outfit 1, I love the colors in the tee and pants, but not in the cardigan. So simply changing to an ink blue cardigan would probably make the whole look work better for me. Come to think of it, I don't know why I'm hanging on to that cardigan. I wear it with a few things, and yet, rather than adding to an outfit, I think it tends to detract. I like your idea of taller boots with the second outfit. The other option I considered wearing was my pewter high-top sneakers. These shoe choices were more about the walking I needed to do than the overall look, I must admit.
gauche, you have offered great insights as well. You are spot-on when you identify the chinos and boyfriend sweater together--and their prominence--as what doesn't feel like "me" in outfit 1. I do love boyfriend and slouchy pants, and I like a long boyfriend sweater, but I usually do not try to pair them! Good idea for an aspiration: aim for something "unconventional in texture/shape and some structure." I think I typically do that in some way, but sometimes other imperatives lead me astray. With the chino outfit, I was trying to dress for the shoes. When I got to the t-shirt and needed a topper, I just grabbed the sweater for color. Your idea of structure made me think of my denim cropped moto jacket as an alternative topper for outfit 2 (see Finds below). I think I'd like that a lot!
Caro, I think I need to get a copy of the Kibbe book! Our library doesn't have it, unfortunately, so maybe I'll buy it. I think I may have exhausted the free resources online. Anyway, I felt much better in the second outfit. In the first outfit, I love the tee and the shoes (too bad they do not an outfit make, in themselves!!), like the pants pretty well, and feel quite ambivalent if not slightly negative toward the cardigan. And I felt pretty frumpy in the outfit, though I kept telling myself it wasn't that bad.