Lisa, why do you go and post things like this on the weekends when I'm off doing other things??
Even reading everything briefly, there's been so much good discussion, and good points made by you and other. I'm not sure I can contribute anything new beyond my perspective, but here's what has struck me.
First, you sound like a woman who knows what she likes. That is GOOD and IMPORTANT. I'm not always that person, and it drives me crazy sometimes; I am not satisfied (with an outfit or even the whole closet) but can't imagine what is missing.
You know your outfit formula! That is fantastic! So why aren't you going forth and accomplishing it?
It sounds like you are very easily influenced by trends. Is this because of your exposure to them in your job? I am not drawn by trends per se, but I definitely am tempted when I go to stores or websites. Without that exposure, would you be content to do your own thing and disregard the trends?
I'm asking because that's what I do. It's what I've done most of my life. And it's weird, because I love shopping and seeing what's new, and yes, I enjoy the rush from buying. I feel disappointed when I shop and don't go home with anything. But that happens, frequently, and largely because I have a long list of things I do not buy.
This is going to go a bit off of what Angie counsels, but in line with what Claire said: Poison eye can be an excellent tool for avoiding what doesn't make you happy. My poison eye is highly developed for (1) silhouettes that literally do not fit me or do not flatter me the way I like, (2) colors and prints that do not make me happy, and (3) materials and cuts that are really uncomfortable or impractical for my life. There are many things in these categories. As a result, I don't even consider:
1. Non-tall pants, trousers, or jeans in stores.
2. Low rise anything.
3. Three-quarter length sleeves.
4. Fitted skirts.
5. Black, gray, tan, or brown anything, with rare exceptions.
6. Tops that reveal a regular bra.
7. Shapeless or oversized anything.
8. Unstructured dresses, particularly in thin, "silky" or sheer materials.
9. Almost anything in suiting material.
There are more, but my mental list eliminates at least 90% of what I see in stores. I can be tempted by gorgeous prints or colors, but the material and garment has to be right as well. I've never been happy with items I got in spite of them violating one of my "rules."
My shopping temptation is tops. It's relatively easy to avoid bottoms, since most that are available don't fit and never will fit my body. But most tops look pretty decent on me, by themselves. I'm far more likely to end up with orphaned tops than orphaned skirts. I have to be strict with myself about cut and fabrication, and know for sure what skirt or jeans I will be happy pairing the top with.
And of course, the result is that I don't look remotely trendy. I'm okay with that, because I like what I see in the mirror. I don't look at Pinterest or bloggers for outfit inspiration. YLF is probably the biggest temptation for me, since there are so many people posting good outfits. I have to recognize which elements go into those outfits that I'm not happy with, and then I can step back.
I also have to say that it took me a very long time to build up a closet wherein almost everything fits my aesthetic. I made do with stop-gaps for a long time. They were useful, because they helped me make outfits while teaching me what I didn't like. Some key pieces I never found at retail; I made what I needed, or had them made by eShakti. And others I just keep on my list for years. Maybe patience is part of this process, too. I'm not sure I was always that patient - my big wardrobe cleanout got rid of FOUR skirts in the same shade of brown, none of them ever satisfactory - but I sure learned a lot in the process.