Lisa, a couple of ideas for prettier at-home ensembles from a long-time work-from-home person:

-Knits/sweaters with an open or dramatic neckline. Could be a wide boatneck, portrait collar, deep v-neck. Soft and cozy but showing a little skin adds prettiness, and having a bit of drama in the cut elevates the look I think. (Maybe would also work with something unique about other aspects of the cut -- balloon sleeves, or a tulip hem. Or maybe lace/pointelle knit? I don't know if all of these would appeal to you but just anything to separate a piece from the ole "I got cold and threw on my husband's boxy crewneck" look, right?)

-Jewelry that is relatively small and lightweight -- a finishing touch that doesn't get in the way as I'm going about my business around the house. Mostly short necklaces and small dangle earrings for me. I type a lot so don't really wear bracelets (esp in winter when I'm liable to be in long sleeves). Oddly, this breaks the small and lightweight rule but I find that larger statement rings can also work well for me (I take them off for cooking/cleaning but they're fine for computer work and general swanning about and it's nice to catch a glimpse of something pretty as one's hands are flying across the keyboard).

-lotions/potions/personal care products. Maybe also scent/perfume for you. This more on the "I want to feel prettier" rather than "I want to look prettier" side of things but I do think slathering yourself in something a little indulgent can really help one's mental state. I have this baby pink watermelon scented lotion that is TOTALLY not my usual thing but perhaps precisely because of that it is rather delightful to use it once a week or so, makes me feel a bit girly even if i'm still hanging around in my schlubby sweats.

…speaking of, Bijou inspired me to wear my blackwatch blazer. I wore it with jeans and sneaker and a tee. Very comfortable. Very functional. Looks fine… And either I’m too feminine or not feminine enough for this look. Maybe a silk blouse would help, but that’s not immensely practical. Or possibly white sneakers. Or maybe it was the jeans. If it were a suit, I think that would’ve worked. I’m of a mind to think this is simply not me…

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.

I have also been pondering this thread - love what you wrote LaPed just above.

I am going to start a thread about feminity at different stages (as I feel differently about it now than I did in my 20s).

And while I don't like to really talk figures and shapes etc, I find it hard to wear "borrowed from the menswear dept" looks because I am not gamine. Those boxy and oversized "cool" looks just make me feel like a box....I think a bust can be hard with casual clothes - whereas with tailored or dressy clothes I feel much more feminine and powerful. In the casual sweater/hoodie it's much more challenging.

I agree Sally . I’m of a similar figure type - nothing gamine about me . I only wish .

LaPed - thanks for such a thoughtful reply ! The Olsen twin comment came off the top of my head , and I do realize that they dress like little men a lot of the time - albeit very rich little men And yes , their clothes are quietly luxurious , which is the root of their appeal ( to me ) . My hair ? It’s not off limits- it’s just a pain in the —- to deal with . It’s fine and thinning and full of cowlicks . I am leaving it alone right now and attempting to let it grow. We’ll see what happens ! I fully support the little things like new makeup or scent , and even a manicure for doing wonders for the soul . I’d love a good Sephora binge right about now

This thread just keeps giving. Reading LaPed's comment made me think of my daughters and how basically androgynous dressing seems to be the thing right now. I do believe this generation is much more aware and open about gender roles as social constructs and are much more likely to identify as non-binary. Billie Eilish goes from Cousin It to Marilyn Monroe and that seems pretty emblematic.
Regarding the Olsens, I think the counter-point is Gucci under Alessandro Michele. So it is either less is more or more is more with no reference to gender.

I love the responses here -- thank you, everyone! Learning lots and thinking lots.

LisaP, you have a lot to chew on! Have fun with adding in the pretty

La Ped, FWIW, as a fashion professional, the way I see it is that "the cultural thing" you are describing is a small facet of current fashion and style, and it's forever changing! The diverse melting pot is growing, and thankfully

Shevia, your example of Billie Eillish is clever! Billie herself went from unkept minimal to MEGA glitzy maximal before she hit pretty Marilyn. Very good Gucci example too. (Btw, have you seen the Billie Eillish documentary? It is SUBLIME).
Hi Lisa - I ran across these sites I thought it might give you some ideas. I particually like the pointelle sweater because the texture is so romantic but they can fit your preexisting wardrobe, velvet, peruvian connection and the anthropologie aesthetic, poets shirt and blouses in silks with drape or lawn with lace, pintuck or emboridery. Anything embroidered. Pins especially floral, sheer and illusion blouses, nili lotan might have some photos as her israeli soldier meets lace blouse might call to you, dark florals (have you looked at brooklyn's outfits lately. enamelled bangles. Consider a motif flowers or birds to build upon, anything by french kande vintage necklaces and ethnic jewelry - dramatic but still feminine. Those were some thoughts. BTW I want a french kande necklace - several for layering....sigh..

Lisa; I'm wondering if you have ever shown us what you wear around home because your WIWs are quite feminine to my eye. IIRC, you have a side that is athletic and sporty. I don't think I've ever seen you in those type of clothes which in general I wouldn't characterize as feminine.

I think of color, any color, as more feminine than an entire outfit comprised of neutrals. Unless it's white or cream.

What about amping up the drama in your casual clothes? Not exactly sure how. . . but drama is more in line with how I think if you vs. femming up.

As to generic? For Asian women of a certain age, it means shapeless ill-fitting, loose clothing that is black or dark and has no texture. Orthopedic shoes and no hairstyle. No makeup.

Donna - this is exactly what I’m trying to do - add personality and femininity to my casual clothes . And I agree that colour and a bit of drama is the way to go . Ortho shoes , no hairstyle and no makeup is so common . I get how women come to that place , I really do . It’s even tempting to let it go and just exist . But I’m not quite there yet .

I think a year or so of pandemic dressing meant “letting it go and just existing” for many of us! I reached a point where I decided enough was enough and I couldn’t take resigning myself to a life in sweatpant jeans. I suspect you’re feeling some of that too. I think you’ve posted some really lovely outfits incorporating colors that suit you just as well as your favorite neutrals do.

Lately I am considering amping up the eye makeup a little bit. I don’t do bold lips — it doesn’t suit me, and then there’s the mask thing. But I feel like with my changing hair color and thinning brows, I’m losing some of the inherent definition and contrast in my face, which is a weird feeling — like my features are starting to fade. So I might start wearing some eye shadow again. You’re really good at makeup so I suspect you’d have a little fun experimenting in that area too.

Lisa, this thread is indeed a treasure trove of advice and I always appreciate how you articulate what may have been niggling at me at a subconscious level, even though I am yet to even admit that to myself, much less put myself out there to the forum. You are one very remarkable and honest person and YLF is an amazing and kind community.

@Gryffin - OMG, once again you have delivered!! I never knew French Kande existed - so fabulous! I always adore seeing what you are looking at. As I am all about chokers at the moment (to hide a rapidly fading surgical scar on my throat), one very fabulous pearl choker has caught my is just so great to know what gorgeous things are out there.

Thank you, Bijou , for your comments. Sometimes honesty and openness gets me in trouble , but it is what it is .

I have loved French Kande jewellery for ever - even though it’s a little ornate for my usual looks . There’s something SO appealing about how it looks layered up . It’s quite pricey in Cdn dollars though , and out of my reach , which is probably a good thing

Ooh, good point about jewelry. I have been skipping the earrings I usually wear because of masks, and realized I don’t have many necklaces or rings. But if you do have some already, pulling them out even for casual days may make you feel more like yourself.

Sorry for late response- here are some items that I either own, or plan to buy. My climate is v different to yours, and companies may not be accessible, but hope it helps.
My style reminder is “airy, modern ease”. If an item doesn’t fit those 3, it doesn’t make the shopping basket!
Suede silk joggers
Suede boots
Gold ear jewellery