Wow ladies, thank you all so much for the wonderful feedback! It's fun to see how varied the favorites are ^^
Suz, I looked back through all of these and thought "would it still work if I was blonde?" but I'll spare you that graphic While it's true that my dark hair is helping offset the dark elements in each of these (and adds some good contrast), I think that they still would work with light hair. In #1, the hat/shirt/shoes black bookend. In #2 the red bookends, and the black from the blouse is repeated in the jacket buttons. In #3 the darker skirt is surrounded by big swathes of light. In #4 the tall boots along with the boots/vest bookending draw the eye vertically. And in #5, well that's the only one I thought might be tricky but I've a hunch the light jacket/top/shoes would be enough to offset. And I'm sure your taupe boots are just around the corner!
Mary, I think I just need to use softer blouses with the furry vest. That blue one is rather stiff so it doesn't always drape or layer well. But I do love that color combo!
Lantana, Joy, and Lisa, thank you for the detailed feedback, I really appreciate it!
E, 58F in mid November is quite out of the ordinary here in the PNW! In fact, we probably won't hit that temperature again until June -_- Looking forward to seeing the results of boxy tops and full skirts experiments!
Isabel, my hair is even darker than yours and I find my light boots super versatile, perhaps even more than my dark boots. You don't need to have a huge amount of light in an outfit, either; having any light element on the top half OR showing some skin (face, forearms) is often enough additional lightness. Adding light accessories can help, too.