I've been loving this whole thread and mulling it over for a while now. I think it's interesting that you mention The Row, because I feel like the Olsen twins' designs are so indicative of a whole cultural "thing" that's taken place over the last few years (or maybe the whole decade, I dunno). Basically, that wearing anything even a little bit "over the top" in terms of colour or pattern or embellishment is somehow déclassé. "Power dressing" these days is all neutrals, all the time (like the early 90s all over again?), and a completely paired-down look has become the definition of aspirational style. (I suspect the tide will turn at some point. In fact, I think it already has in home decor; I'm seeing a lot more love for clutter/kitsch/jumble than I was a couple years ago -- perhaps it stems from lockdown life and actually living in our homes?)
I remember reading an article that described The Row as "Uniqlo for rich New Yorkers" -- the place where you go to buy a dozen identical sweaters so you don't have to think about which sweater to wear. And I remember one younger Row fan (someone in her 30s) being like, "Will I regret that I'm dressing like a 60-year-old while I'm still in my 30s? Yeah, when I'm 60 I'll totally regret it." I'm paraphrasing, but you get the idea. Totally understandable for the rich/famous/powerful to want to disappear in the most luxe way possible. But for the rest of us? It's okay to announce yourself a little every now and then, to be bold instead of fading into the background.
One thing you wrote that really struck me is this: My casual wardrobe is where this is really evident. Everything is neutral and basic, and feels like it could be interchangeable with my husband's if we were the same size.
I run into this too. My husband and I dress largely in neutral, natural fiber, jeans + top combos. It's easy to end up twinning and that's a little weird! I've realized that really "getting dressed" for me involves putting on at least one thing that would make my husband roll his eyes. Sometimes it's lip colour or perfume or doing something with my hair, sometimes it's a skirt or big pleated pants, a floral pattern or one non-essential accessory. Actually, that "one thing" is usually something my mother would roll her eyes at too. I didn't really have any reference point for "femininity" as a kid. Jeans and crewnecks -- fine. Anything else -- frivolous. And really, doing that one extra thing is usually enough to make me feel like I'm in an outfit rather than just clothes. I think your bar is higher than mine, because you already have impeccable makeup/nails/etc and your accessory/jewelry game is so strong. I definitely don't read the looks you share on the forum as androgynous or basic -- far from it!
Last thought (I've rambled enough): I know you said hair isn't an option right now, but it's definitely something to think about. My main motivation for growing my hair out was that my go-to pixie and blunt bob styles were feeling too severe. Going longer, adding layers, and encouraging natural texture/soft waves was my solution, but I think you can stay short and still achieve a softer look, à la Angie. Something to think about, when you are able to get back into a salon. I also switched up my perfume at some point over the past few years, and went from androgynous/resinous scents to a predominantly rose fragrance (Améline from Phlur), and it was sort of transformative. Wearing an all-out tomboy outfit with a rose perfume is totally different for me than the same outfit paired with, say, CDG Wonderwood. Sometimes it really is about the feel rather than the look.
