There appears to be a style meme going about, and I do put way too much thought into my clothing, so here's what I (currently) tend to wear:
Lots of black, but also grey purple pink and dark burgundy red. Very occasionally some off-white. Nearly all of it comes from thrift stores. I want to have enough layers/texture for the eye not to slide off me, but not so much detail that the outfit looks fussy.
Although I sometimes try to wear them, I've never really been comfortable in trousers. Right now I'm mostly wearing knee-length skirts with leggings - this works especially well if both skirt and leggings are black - the leggings elongate the look without being as formal as a long skirt; also if they're fairly thick jersey and end at the widest part of my calf they make my legs look better.
I usually wear fitted (but not skin-tight) tops/shirts. *Sometimes* layered. I'm pretty small-chested but recently bought a sports bra, which I'll probably wear for warmth this winter once I get used to the shoulder straps. I don't wear clothes with writing on them; although I'm occasionally tempted to embrace the fake-vintage-T-shirt fashion, I seldom see anything with a slogan I like enough to put on my body; too bad, in a way, as I like decorative lettering.
I gave up on pierced ears a decade ago (one of my lobes kept getting infected); I have assorted clip-ons from the local flea market, but they're usually just as painful since they have to grip hard to my ears to stay on. Lately I haven't worn necklaces much either, so my jewelry consists of family-affiliation rings, ie wedding band and engagement ring on one hand, and an emerald ring my parents gave me on the other. All three are pretty streamlined in design.
Shoulder-length hair, down or tied back in a ponytail. Sometimes I colour it purply-red, but I noticed a couple of grey hairs earlier this year so I'm waiting to see if I get any cool Rogue-like streaks. I have some shimmery Burt's Bees lipgloss, some NYC Color lipsticks ("Pink Sand" which is basically the same colour as my lips, and a plum colour that I sometimes use as eyeshadow ), and a cover stick. I also have assorted bottles of nailpolish, but haven't used them lately.
I found a faux-fur trapeze coat at the Goodwill a few months ago and have brought it out for winter. With the leggings it looks sort of 1950s Bohemian. I own many weird hats, mostly knitted by me.
Where I go for ideas:Style Bubble
, You Look Fab
Addendum: Shoes and Purse
I prefer shoes with at least a bit of a heel, because a) I walk on my toes anyway and b) people can say what they like about pumps - the majority of the really torturous shoes I've encountered have been innocent-looking flats, that when worn either rubbed my heels raw or fell off my feet with each step. Since September I've been wearing low-heeled black shoes with straps that fold back so they can be either pumps or mary-janes. Last winter I finally found boots that were both comfortable and non-ugly in the form of a cheapo pair of black, slightly futuristic zippered ankle boots.
I have various medium-sized purses in various colours. I've found it's best if they're structured, with lots of interior and exterior pockets, because they're sort of my little portable office, what with carrying my cel phone, pills, wallet and all my stuff. I think it looks sort of twee if they match my shoes, so they don't.