I am totally overwhelmed by your kind and helpful comments. I am really glad that the sandals and boots are already prompting me to push my style forward, and the positive feedback makes me thrilled that I'm heading in the right direction. Yay!
I think the struggle I'm having is that I feel at home in the "new" outfits I'm creating, but in comparison I feel pretty boring in what used to be my "go-to" outfits in the past - i.e. what I wore on Monday and Tuesday. I'm glad to know that for the most part there isn't a major disconnect between the "old" and "new", but I'm VERY grateful for the suggestions to kick them up a notch, too.
JewelryGirl, a BIG thank you for stepping in and offering so many suggestions about how to wear the necklace. It won't fit over my head it I try to wear it "open", but I think you're right about wearing it with a higher or narrower neckline. The pendant idea sounds great - I don't have the right pieces, but I'll query my bead-savvy aunt next time I see her to ask if she has any ideas. I'll have to see if it works as a bracelet - the length *may* work.
Shiny and Planetamy, you have such creative ideas about colors.
The green dress: I think you both have it right that I need to add more color contrast. Last time I paired the dress with turquoise and yellow and I think it worked better. I haven't considered purple, coral, or the cream moto jacket, though. GREAT suggestions - thank you!
I never would have thought of wearing red shoes with the Mother's Day olive dress - I initially was going to wear my yellow canvas peep-toes, but the day turned out too cold & I didn't want to ruin the shoes in the rain. I also like Lena and Shiny's idea about adding a cream handbag. I haven't run across one that I liked well enough and was in my price range (I don't spend very much on handbags, ever) but maybe that's something to keep an eye out for - it's unlikely that white or cream handbags will go out of style any time soon. (I've mostly been using my slouchy matte fuchsia satchel for the past several months.)
Angie, thank you in particular for your enthusiastic feedback! I think the main difference in the past week was that I felt "at home" in my casual weekend wear without feeling or being told that I was too dressed up. In the past I would have worn ballet flats instead of the Brulees or the boots with both outfits, and I'm amazed at how changing up my footwear adds a very different element to my look. I felt a little uncomfortable on Friday (the green dress) and yesterday (the red jacket with butterfly pin) because the layers I tried didn't jibe together as well as I'd like. However, I didn't feel like I looked awful - more that what I was wearing wasn't "a 10."
Thanks again to all of you for your feedback and suggestions - this is incredibly helpful.