N, I have really been enjoying your posts. You definitely have the opposite problem to what I came to YLF with- which was an overstuffed wardrobe of about 200 pieces which was about 10 times bigger than your current approx 20 pieces in this thread. But how I had ended up like that was partly because I didn’t do the work you are currently doing. I had gained a lot of weight in my late 40s and was desperately trying to clothe myself and feel better by buying pretty things but so many didn’t work, and then I felt guilty and wouldn’t cull. It took me 8 years to build that overstuffed wardrobe and 5 so far to get it more useable.
To answer your question about silhouette, I am not sure that I have a preferred one although I do prefer skinnier bottoms as my favourite era is 80s for pants- when I was in my 20s having the time of my life. I definitely have a style though- Kibbe “theatrical romantic” resonates and definitely some sass. I like there to be interest even in a simple silhouette.

You are putting in a lot of work on this and making smart choices. Justine Leconte’s videos are good—I’ve watched several since you posted the link for the swimsuit one in my thread. In the end, when you finally get your hands on some clothes, I hope they make you smile.

For the basics, you might want to make an appointment for a fitting. I’ve done that twice in the past 2.5 years since we moved here and my swimsuit appointment is in one of those lingerie shops. I suggest it because Japanese sizing and ideas about bodies might make it frustrating to shop there even though you can fit into the bras. The SA can guide you through some of that.

My youngest is 2.5, so I can relate a bit. My style has certainly flexed as I've had to accommodate parenting and body changes!

I have found David Kibbe useful as a jumping off point, although exploring and learning can't be substituted!

I like to stick to soft and drapey things. I like to have a waist, but prefer it to be alluded to rather an emphasized. I like a strong shoulder, and for separates, I prefer shorter length tops and higher waistlines most of the time. I don't like things that are too straight or narrow, most of the time. I like to stick to cool, lush colors and makeup, but I'm not overly strict about color.

You can read my Style Cues in my Profile. I've tweaked them very slightly over the years, but they haven't much changed, to be honest.

My signature silhouettes are based on what I can tolerate physically from clothing and what I want to show or hide. I hate wearing an underwire bra so I won’t wear anything that doesn’t work with a bralette. I won’t wear anything that requires special underwear like shapewear and thongs. Nothing against those items for others! I am just very fussy with the feeling of clothing. I am right on the verge of petite, but not actually petite, so long flowing pants and maxi dresses tend to overwhelm me. I am thin but gain weight in my stomach, which at my age leads to a lot of seriously rude questions about pregnancy, so I avoid anything that gives a baby bump look. I don’t really consider my silhouettes to be based on my style preferences. They’re based more on my body preferences, if that makes sense.

I was spending some time this afternoon playing with my Pinterest boards and thinking through future purchases and, though I don't have a signature silhouette, I do think I've settled into some signature outfit formulas. Those are:

1. Black dress with sandals or boots. I have black dresses in a number of different silhouettes, which keeps things interesting for me.
2. Column of black with interesting topper. I don't do a lot of big, bright contrast, so "interesting" for me is something like another neutral or a dark floral.
3. Blue jeans with black top and brown accessories. Or black accessories, but only when I'm being particularly lazy.
4, Statement outfits. A very small percentage of my closet is what I'd call "statement outfits" that are something different and don't fall into any of the above categories. They're a little something special.

These are all quite different from what I would have considered my outfit formulas when I first started on YLF, so it's evolved over time. One advantage of keeping a relatively small closet is that you're free to make changes as clothes wear out and leave your wardrobe.