Sorry these responses are so late; I wanted to reply to everyone individually but for now am just posting this as-is in hopes of getting back to respond to those I've missed.
Shannon,
pieces are from last year. Trousers and tops seem non-descript, never particularly on trend. Yes, the cardigan was too much drape. Previously worn only as loungewear with leggings, so it already has a strong homewear-only association for me.
Meredith,
glad your sense of humor appreciates my occasional morbidity.
Rabbit,
pointy silver shoes! Yes. Your observation about Greyscale's style is helpful to me, although she and I have very different body types.
Greyscale,
your point about one's own feelings clothing getting in the way of seeing how an outfit actually looks is well taken. Perhaps I should get back to taking WIWs even though I don't plan to post any more of them.
Laura (rhubarbgirl),
my "visible parts" are all well-cushioned, not much visible structure there. Bold jewelry as far as earrings and necklaces isn't really my thing. Belts, rings yes. Would those help? Statement jewelry riles bf's poison-eye, along with hardware and all things flora or fauna. "Barely a step up from pajamas" perfectly describes the cardigan, which was bought as and will remain loungewear.
gradfashionista,
you're right, these pieces cry out for footwear with character. These sandals (pictures attached) I love for their quality, fit, support and so on, but they don't *say* anything and they're not on any trend. I have yet to figure out how to tone down the unfortunate boho garnish.
Suja,
"Upper West Side Therapist who has given up ..." Oh my! For structure, I swapped out the lounge cardigan for a black/white graphic wrap top which I didn't think would go with grey, but it felt much less dumpy. And I got compliments on ... my hair.
Liz,
"I wonder if there's a psychological thing going on here as well as the practical aspects."
YES! Until a few years ago, I lived in suits. Dark suits. (At one conference I dared to wear a medium-grey pinstripe suit with burgundy print wrap top and burgundy spectator pumps, and was mistaken for a member of the press. Never again.) Then my life changed, I upgraded my lifestyle by downgrading my work to a field in which I'm self-taught and am avidly avoiding any management responsibilities. Worn baggy clothing fits fine with that, but doesn't reflect the range of options I actually have. Oh, and I had a sports injury and gained a lot of weight, so I'm dressing a different body than I know how to work with.
crackers,
you're right, I won't try head-to-toe EF again. Love the contrasting racer back tank idea!
lisap,
I haven't seen any of the EF ads, just heard about it here. "looked like crap on me, and makes me feel the same way" is true for the cardigans. Even as loungewear, they feel too sloppy to me. I'm probably better off with decent-looking fleece, or a firm jersey jacket.
Diana,
I'm 5'6" on a good day. IT with long torso, short legs, full chest.
Firecracker,
color is such an important point, thank you for that insight. I wear a lot of grey and black, and when combined badly it's just drab.