Hi Deb --
Suz said so much of what I want to say re stretching/discovering/evaluating.
I wanted to add that sometimes the pieces I buy to shake things up a bit get worn immediately, and sometimes they take a little longer to worm their way into rotation. Usually that latter is due to not putting the new things with older things that feel like me and/or getting things to work proportion-wise...but when I get the click it's a good feeling (and nice to have something different than one of my "uniforms!"). So hang in there for a while longer and keep experimenting.
-- I'll come back to #1/2 but I love all the outfits with the cowboy booties/denim skirt; they look very natural/effortless on you and look intentional...like you put some thought into them. Again dittoing Suz on your great legs. I also think these tops in warmer, earthy, not-too-intense neutrals look really great on you (a tough feat as many of us look like death in them!).
-- I actually like the brown/ivory booties on you and especially like them with the lattice top since they echo the texture. They aren't bad with the denim skirt, but because they're more delicate I wonder how they'd look with something a little softer/drapier. A knit skirt? Your jean shorts if they're worn in/faded? I don't know what's in your closet but maybe there's a little something to try.
-- Back to #1/2. I like the idea of all the "stretchers," but (sorry!) it's my least fav of the bunch on you due to the brighter color and high contrast...it seems to fight with your personal coloring.
I wonder what would happen if you tried one of your Ts with the shorts/black booties? I could see a darker graphic T being kind of cool/oh I just tossed this on, ha. Personally I'd try the two tops here (4/5) and see how it went. Nothing to lose, right?
Keep us posted!