*a larger crisis in my life about how I manage my time, my energy, my space, my leisure, even my mental space*

Big hugs from me too. I don't really have any brilliant thoughts to add to everyone else's brilliant thoughts. But I just wanted to say I really sympathise with the statement above. It's... and now I have to laugh, I'm so sad, haha... I'm really proud of myself for doing one thing a day, like a load of laundry (and note folding doesn't happen on the same day EVER). I don't know why it's so hard to get things done and make them stay done! (Please no one point out to me that every day there will be a dish to wash, that that's the nature of it... I do not believe this. When I wash one dish, this should mean all my dishes should now be washed forever and ever.)

I have been doing the big purge after downsizing homes for 5 years now. I'm still on clothes. I haven't touched magazines or kitchenwares...

Not to scare you or anything about how long things can take...

rachylou, Yes, everything feels like Sisyphus work... And I fear that I get so caught up in these tasks that I forget how to enjoy life and myself. When is the last time I went to a movie theater? Read a novel? Went to hear live music? Things I used to do not just for pleasure, but because they enriched me and made me who I am. Or was...

I think you need to give yourself a break. (hug) Seriously, they're just clothes, in the end. No need to go crazy over wardrobe building. These things take time. I vote try to enjoy what you have in your wardrobe right now. Build a few outfits you really like and repeat those as often as necessary. Store the other stuff you rarely wear elsewhere and add items back into the wardrobe when you use them. Think about where you want your style to go and take care that future purchases fall in line with that, but don't hurry to buy anything and stick to your budget. It might take a while, but you don't need to figure it out all at once. There's no "perfect" wardrobe anyway.

Have you considered going through your closet and perhaps consigning many of the items you no longer wear? Shoes, clothing, bags, etc. This might give you a few extra $ to put toward your budget.

I believe it makes sense to start with the best basics you can afford. A couple of nice pants (or jeans), several solid tops or t-shirts (in basics, such as white, black, light gray, and include a stripe, as well). These basics can be layered under a cute jacket (or two as the budget allows). Once you're able to add to your wardrobe, it would be great to purchase a few jackets ~ navy, white or cream, and a black jacket. I think texture can create so much interest to an outfit, so it would be nice for the jackets to be in a tweed or have some interesting, brass buttons (on a navy jacket). This is a personal preference, but I believe that jackets are a lot cuter and more feminine when they have a 3/4 sleeve. That way you can also show off some cute, stacked bracelets or bangles.

Then comes the fun stuff. Accessories really are the icing on the cake. Start adding in some belts (basics like black, chocolate brown, and nude) and an animal print. Belts add so much structure and polish to an outfit. Add a variety of shoes suitable for your lifestyle in black, navy and nude or metallic ~ ballet flats, pointy-toe pumps, wedges, flat sandals, etc. Add one pair of shoes in an animal print or snakeskin that can add some pizazz to a jeans and jacket ensemble, for example.

A variety of scarves is another easy way to add color to the combinations mentioned above. Scarves add interest, polish and texture (see the Eileen Fisher website for the video showing unique ways to tie a scarf). A long necklace is another way to really pull an outfit together.

Good luck, and please give us a progress report!!

Astrid, I think part of my issue is that the clothes came to symbolize a lot of emotional stuff, and so you are right that I made them more complicated, heavier, than they should be.
LGS, I will have to check out the video! I love scarves, that's the one thing I have in plentiful and happy numbers.
This past night I went to bed thinking how nice it would be if I could actually have a personal session with Angie; then I had a dream that this came true. So thank you Angie for your compassion and empathy--thanks everyone for that--and of course for all the wonderful fashion advice.
Then this morning the point about my ill-fitting and outdated wardrobe was driven home. I was wearing a beloved purple light-wool jacket, which is more than a decade old (sort of a cropped peacoat). I was also feeling painful pangs in my stomach, and being a bit of a hypochondriac I thought I had an ulcer. It took me an hour to realize that the jacket was too tight. As I mentioned earlier, after pregnancy my ribcage went from a 32 to a 34. The change is small enough that old clothes still fit, even buttoned up, but some are ever slightly too tight. I laughed at myself as I unbuttoned and released myself from the pain in more ways than one...
And LGS, great point about consignment; I've done it in the Fall for the first time and I will do it again. (Just not this jacket. It's a cherished gift from my mom, I might have to store it in a box of personal treasures...)

PS. Somewhat of a dumb question, possibly to be posted on another thread. Where do you find good images of outfits for "harvesting" for Pinterest?

Well, I was going to ask if you are transferring some emotional distress or other problems to your clothes, but you already answered.
I may be imagining things, but it sounds like you went for a huge life change and your inner self is still adjusting. Maybe you are having issues trying to conciliate your "old self" with your new life?

Back to your wardrobe, I guess you are plenty of good advice right now,

but I think you probably should start buying things instead of waiting, just do it slowly. Same way you are transferring emotional stuff to your clothes, the way you feel while dressing will affect your personal feelings about your life too.

Feeling comfortable in your clothes will help you to feel more at easy with your life.
Star by cleaning/reorganizing your wardrobe before anything else, to see what you actually need right now. I would start separating things in 3 groups: what I really don't like or can't be used anymore, things I really like and will keep, things I don't hate but don't like either or with fit issues that can still be used (we usually can't afford a entire brand new wardrobe, so it's wise to take it slow). First group should go away - and maybe some pieces can be exchanged for other things in a thrift. From the other 2 groups, examine what you actually need and just try to find something inside your budget that: 1) work for you (shape, color, etc), 2) work with things in your "I like" group, 3) prefer basic stuff. Since you are still adjusting/having doubts about style, avoid too stylish/trendy things - basics will be needed in any capsules you built in future and they will work with any style you choose afterwards.

A last suggestion, don't do that on a day you are particularly more dissatisfied or stressed neither do it with an empty stomach or after eating something you don't really like. Sounds silly, but food really affect our satisfaction/dissatisfaction feelings and a dissatisfied stomach will increase your shopping impulse - and the odds of shopping something you will regret later.