Thanks everyone. This has really helped me get out of my head and into another perspective on what I'm trying to do.
Kathie - yes, great idea to start with hair/specs. I grew out my gray about 2.5 years ago culminating in a short chop that wasn't really great (but got rid of the color) so I've been in a rebound growing period for a while. And I think specs can add dimension as the gray does fade me a bit (i know-- lots of other forum posts on that topic).
Jussie - good point about shoes. The black ones in pic 2 aren't helping are they? I've reached the point where I can't wear heels anymore, so moving to low heels and flats. Also finally coming around to good quality shoes. I have a wide range of red shoes
Cardiff girl - the jacket is actually a purple velvet so not as dark as it looks, but agreed re: color. I have a couple deep fuschia tops that I like quite a bit. I also have gravitated to olive as a dark neutral. The sweater in 2 is navy, which is a color i like less, not sure why. I struggle with the body shape, I'm either an x or 8 and my shape has shifted a bit with this impending birthday!!
Kkards - Thanks for the feedback on 1 vs 2. Proportions are something I'm still working through. Yes, my office is business casual, leaning to casual casual but I like to dress it up a bit.
hgr - thanks for the comment. I have done the closet clean out, I rotate my stuff frequently and love accessories. it's sometimes hard to get rid of stuff because sometimes I like things again after they have been away for a while. I tried to do the 333 closet for a while, and narrowing choices helped , but i never did a good job with the seasonal planning.
smittie - GREAT question about why I want to change. I have always been very casual but as i get older, and with the gray hair, I want to look more thoughtfully put together. I want to look fresh, not frumpy. I am low maintenance but am FINALLY coming to realize that looking stylish and put together doesn't just happen, it takes time and planning. And LOL yes, it's February, which here in NC is the start of spring and big temperature changes which make getting dressed even more of a challenge.
Unfrumped - yes, i'm in the middle of a project where i photograph my outfits at work and save them to a pintrest page each day so i can assess them in their natural habitat. Good point about certain items working better with some things instead of others. Sometimes I feel blah in a piece and then put it aside, instead of trying it with something else. I'll have to work on that.
Krishnidoux - I like both your suggestions - yes, I should go explore a single store or line. Especially as I like the idea of a work capsule that just works, where things go together. A lot of my wardrobe is culled from separate separates. Your point about "what is this jacket supposed to go with" is also a brilliant question. I don't know why i don't think of it that way, it's more hit or miss with me.
kellygirl - thank you for persisting against technology! Yes, my pintrest board has been helpful in evaluating outfits.
Suz- thanks for the links. Also for your story about patience. I am pretty impatient to get this sorted, so it's a good reminder that this is a process.
Angie - thanks for the link. I definitely need to take it one step at a time.
I think I'll start with hair, as I have an appointment soon, and then move to an outing to the stores to try a few things on.
Thanks to all of you for your uplifting words and encouragement. This really did provide a new perspective for me to get started on.