You've all given me a lot to think about. I'm going to start another thread to discuss some thing I've been thinking about more in depth, but for now...
Diane - It sounds like we lead similar lifestyles, working at home in a semi-active creative capacity, and being moms to older boys. I'll be watching your casual outfits for inspiration!
smittie - I love what ruching does for a figure and have worn a lot of it in the past (and present), but I also find myself gravitating away from the look of it, in favor of cleaner lines and simpler tailoring. I'll have to think on this.
Sarah - I'm liking the olive and black, too. I'm glad olive seems to be coming back into style, probably because I have such fond memories of it from the 80s, safari-themed version of Banana Republic.
shedev - That makes sense. I have made a couple attempts at drapey tops, but I feel like they make me look bigger all over. I'd rather accentuate my smaller top half, so maybe something body-skimming rather than body-con.
Word Lily - I've been pondering this and have some thoughts, but I'm going to address them in another thread, because it's a lot. In short, you're right.
Meredith - I like that tank a lot! I'm not buying rayon anymore, or I'd be trying that exact one, for sure. I'll look for something similar. I think that might be a good solution, both for summer and seasonal layering. And yes, vegan seems virtuous enough. Those cupcakes totally shouldn't count.
Elly - Thank you for the detailed response! I'm in a different boat than you, because I work from home 95% of the time, so don't have the same needs for professional attire. I'm actually more likely to dress up on weekends, when we have social engagements. This weekend was supposed to be an exception, but as it happened, we did end up going out yesterday, and I had to change. I'm interested in your comments about the necklace, but I'm not sure I agree. I don't have pierced ears, so it's a rare day I don't wear a necklace or cuff, even when I'm hiking or cleaning house.