Don't you dare get rid of #8! It looks amazing --crisp and fresh even in the heat (but then I'm always a sucker for a nautical look).
Now, let's talk about #2. I don't see matronly, just a lack of imagination. As is, too much of a muchness. Try adding some light or metallic contrast: a scarf, pendant, belt? I guess your eclectic mix doesn't skew as far as RATE or boho (your casual looks have more polish than my professional ones) but what would happen if you leaned a little bit in that direction?
Next., split up the pieces. Try the top with white or navy capris or slim ankle pants. (Is it a muted print in burgundy? Hard to be sure on my small screen.) Now, try the skirt with a shell or elegant tank, in a toning pastel or dark, but shorter than the original top so you play up the maxi/long legged proportion more. A mesh or lace topper might work over this too. Also, if the skirt is wrapped, is it possible to wear it sort of unwrapped /open at the front, over cigarette pants? (I am picturing a "hostess outfit" for the casual entertaining I imagine as your lifestyle. Please don't disillusion me, I am trying to anticipate my own retirement...)
Sorry to be so bossy but I love the versatility of two piece outfits because they can pull their weight as separates until the next time matchy two piece dressing has a moment. And it's still having one now, or is that over already?