I love the look and comfort of sack/shift dresses, but they make me look frumpy dumpy. I keep trying, however!
Bendable flats, i.e. any flats other than clogs, due to hallux rigidus. All those beauties I see y'all wear!
Most other shoes, esp. heels and virtually all boots due to fussy, hard to fit feet. But I still try and have an array of two and four hour footwear. (The six and eight hour ones are my various clogs.)
But I'm also thinking of the things I DO wear that some of you have listed:
Chambray shirt and white shirts: I had to try on dozens to find ones that fit in the shoulders and didn't gape at the bust. I had to enlarge and lengthen the darts on the chambray shirt.
Scarves: I have a gazillion. I get cold if I'm wearing anything collarless so I need something on my short neck. I'm returning a zillion I ordered from Nordstrom because the newer ones seem to be bigger and therefore bulkier and take up too must neck and chest real estate on 5' 1" me. I keep trying, however. But I hear you on the fuss factor. I don't want my scarves to turn into bibs, and I'm not particularly neat/careful.
Belts: But they can fight with the aforementioned scarves as well as necklaces but are needed to keep pants from sliding down the pancake butt. And they tend to show wear all too soon.
I keep reminding myself of what I DO have (a waist!) and what I CAN wear (short regular size skirts and dresses) and that my only clothing challenge (other than footwear) will be a MOB dress and MOB shoes -- which will be years and years from now if at all since DD's fellas last two months at most.