I'm finally sitting down and reading through this whole thread -- what a treasure trove of advice. I thinking pushing oneself to come up with a set of descriptors and a moniker (and accepting that these aren't something set in stone, that they'll have to evolve with you over time) can be hugely helpful. Angie's suggestions for you are so evocative, I think it's really just a question of deciding which direction you want to take.

I'm thinking that there's a sort of ruthless artistry to a good closet edit. Knowing what to leave out, how to pare down and get to the essence of something, is so fundamental to good writing/art/music, that it makes perfect sense that style would be the same. So, yeah, you're a Style Virtuoso, and I hope you find the perfect summer refreshers.

Oh, and I wholly endorse buying pants, jeans especially, in a couple different sizes when you find a perfect pair -- I've started doing this shamelessly over the past couple of years. I was really resistant for a while, for all those same vanity/body-image reasons, but then I started shopping vintage pants and it really hit home for me that the size on the label is completely and utterly meaningless. What counts is that the rise is just right, the legs are cut just right, the pockets are in just the right place, etc. I think this strategy works well if you want a core set of classic pants you can rely on for several years going. If you chase pant trends it doesn't make as much sense to duplicate heavily, but pants-shopping is just too time-consuming for me to embrace every trend that comes along.

Next step:

• Show us your bottoms that fit on a separate thread. No need to try them on. Finds or photo on the bed is good.
• There is a white jeans round-up, so start there.
• You will need to bite the bullet and order some stuff online, but VERY carefully. We don't want you going back to a store, getting stuff impulsively you think will do, and disliking it the next day or week. Try to break this shopping habit. It's fine when that happens once in a while, or you want to test something at home with the intention of returning it if it doesn't work. We all do that.
• What happened to the skirt you bought? Have you tried it on again?

ETA: you have to think about black and its role in your wardrobe. You are enamoured and seduced with a heavily black wardrobe when you see it on others - and buy a lot of black too. But I'm not convinced it makes you happy.

I stalled on the style descriptors thing for a long time too. I finally bit the bullet and picked out some words and it has been immensely helpful. "Feminine but not girly" has been a key concept, as well as "sleek", which helps me to avoid all those cute tops and shoes with bows and ruffles which inevitably drive me crazy and I never wear.

I had to take everything out of my closet last summer because we were putting new flooring in. I purged tons of stuff since I had to take it all out anyway and it was a great feeling. I also keep a woven hamper in the corner of my bedroom for donate-able stuff. If I try something on and it doesn't fit or I realize I don't like it anymore and I'm never going to wear it again, it goes straight into that hamper. When it gets full, I bag the stuff up. It's not just for me either - the whole family puts stuff in there.

I'm super late here and everyone else has said everything that needs saying, so I'll just congratulate you on doing this again -- it's hard work and brings us up against our shopping flops, but this is going to be so useful.

I love Angie's suggestions for style moniker -- Trendy Classic...hmmm, I like that one for myself. Definitely go with the idea of juxtapositions.

There's also something special to be said for the monikers that describe a persona, like Gryffin's Professional Princess of Darkness -- something about its referring to a character makes it a bit easier to ask the question she mentioned asking herself...Would an X wear this? I found it really helpful when I identified myself as Urban Prince. That's not my current moniker and I really need to work on a new one -- that's why I was talking about a "reset" I think. So I need to do what Janet described -- not just the edit for fit but that added question: Do I wear it and feel great in it? If not, sunk cost and move on!!

Thanks for sparking these thoughts and good luck with your shopping!

Life has kept me from regularly reading the forum the past few months, but I have to pop in and say “YAY YOU!”

I will read whole thread later because my quick glance shows it filled with wisdom. In the meantime, how about a t shirt like this?

Lisa, those tops are the Elizabeth Suzann Georgia Tee in their wonderful heavy linen.

Right now, their turn around time is 6-8 weeks!! Hope that comes down soon. I only have one order that I’m waiting for, and that’s a pair of their Andy Trousers in flax colored linen. I hope to have them by mid-June.

Dakotacheryl - not to hijack this thread but I'd love to see how some of those Elizabeth Suzann pieces look on you. I'm very intrigued by companies like this.

Oh, how well I know that "moving target" you speak of! It sounds like you're doing a very disciplined and thorough job of making your closet work for you. I'm about to do a seasonal change-out, too, and will be keeping your no-nonsense approach in mind--very inspiring. Good point about the style descriptors--really must get on that soon! I just had my hair cut VERY short again, so that will be affecting my choices. I'm going in the opposite direction, for example, with t-shirts. After avoiding them for years in favor of loose, feminine blouses, I found myself craving the slightly tomboy look of a casual jacket or blazer over a graphic tee. Didn't want to invest a lot in this experiment, but ended up finding a few inexpensive, nice-looking cotton tees and tanks from Uniqlo and Old Navy. What I learned when trying them on was the importance of: 1) Neckline--no standard crew-necks allowed; they must have a more flattering slight scoop or V; 2) Fabric content--no spandex, lycra, polyester, or any other cling-making ingredients; they must have a soft, loose, natural cotton drape; and 3) Color and design--they must do something interesting for the jacket I intend to wear on top. These pairings would not work for a professional look, but have been a fun change. My Jeans Problem sounds pretty much identical to yours, though I was lucky enough to find good white jeans last year. (Could current styles have something to do with this? I know what I want, but finding them is so difficult!) Must admit that buying a couple of pairs of non-stretchy jeans in a size bigger than I really wanted to wear has vastly improved my temper...
P.S. Have you tried stretching those white loafers? Angie has detailed several ways to do it that might be worth trying.

Angie - how is it that you know exactly what I would do (and actually did today) ? Yes, you're dead right. It's a shopping habit I need to break. i just don't have the time to spend hours in a mall or on-line.

I'm mentally exhausted by all of this right now - and trying on a few pair of pants today made me want to cry. I'll refocus on white jeans only for right now. My new skirt? Ha. To be honest, it's still in the bag wrapped in tissue and I haven't looked at it since I bought it . I'm not sure I have the right tops for it. Sigh. I had bought one to go with it at the same time I bought the skirt, but ended up returning it. This whole process really drains me. I'll be trying to carve out some quality time (unrushed) to shop next week. Thanks for the ongoing ideas and support .

AviaMariah there is a whole website just for posting Elizabeth Suzann photos and size information. I have posted a few outfits, but there are many many others, in a variety of sizes...v cool.

The only thing to be aware of is that there were some pattern adjustments last fall and some sizes changed. The newest sizing is with Generation 4.

https://www.esstyled.com/