Boot cut low-rise jeans that are slightly tight fitting (esp on the butt. I gotta show off) and a gold or silver/metallic grey t-shirt with a cool design on it (my favorite one has a whale crushing a city.)
Cool weather: Boot cut blue jeans, pull-over sweater or turtleneck, loafers and a blazer (with matching beret) or denim jacket.
Warm weather: Denim or khaki capris, summer sweater or polo shirt and sandals or white canvas shoes.
Add silver hoop earrings, a silver bracelet and rings and there’s my look.
I am a creature of mood.
I wear a lot of long full skirts in the summer. I had to give up my peasant blouses though. Traded them for something with sleeves that didn’t make me look like I was in costume. Shoes – wedge sandals or ballet flats depending on the skirt. Love big earrings, exotic wraps and scarves and being a total cliche.
Or I can wear a Harris tweed three piece suit (the skirt, not pants) with a silky blouse and loafers. Zeldar said recently that this looked “marmy” – meaning like a schoolmarm.
Or I can wear my righteous cowgirl boots and jeans.
My latest acquistion: lamb houseshoes. I don’t mean like Persian lamb. I mean like Lambchop.
Back when I was alive:
Levi 501 button-fly jeans.
Ramones T-shirt
A cigarette
A cup of coffee
Bare feet (summer) or work boots (winter)
Gray fedora
Now that I’m old, fat, and agoraphobic:
A 1984 Paint-A-Thon T-shirt
Jersey sweats
My father’s old plaid flannel bathrobe
$4.97 Target brand canvas flats
Male, 36.
When I was in my teen years, blue jeans, a T-shirt (usually something hippie related), and sneakers.
Now, blue jeans (in better shape than I used to wear, but still frayed at the cuffs), a long-sleeve button shirt open at the collar, and black casual shoes.
Of course, what I’m probably best known for at the office is wearing something more like this:a helmet, cycling shorts and a T-shirt with a zipper down the front.
Depends on who is coming. If it’s my friends from Rocky it would be either a corset with fisnets and a short skirt slit all the way up one side or pleather pants with a bra and a fishnet shirt, both usually with boots with a spiked heel, though occassionally Nine West heels or stillettos. If they were from classes then black pants/jeans with a black band/concert/theatrical show shirt. (One day I wore my yellow blue sun shirt and the entire day people stopped me to comment on the color. “you’re wearing yellow” they’d say,as if I didn’t know. Not one of them stopped me to comment on how awesome Firefly was. le sigh ) If they know me from the thetare it would be blacks, completely and utterly and the socks better go past the ankle and be black too.
Jeans, t-shirt from Threadless (untucked), Doc Martens.
Unless I’m at work, in which case it’s a plaid button-up from LL Bean, khakis, and the Docs.
Black Levis, running shoes, the loudest Hawaiian shirt you can find. This is the default. I got married in a Hawaiian shirt. I go to funerals in a Hawaiian shirt. I will be cremated in a Hawaiian shirt. Just to throw my students off, some days I wear khaki Dockers instead of Levis (Born to be wiiiiild…).
Black slacks, colored blouse, three inch heels, briefcase, silver jewelry.
Usually the typical Abercrombie look.
Summer: T Shirt, cargo shorts, flip flops. I don’t tend to wear hats much, however.
Winter: polo or long sleeve with sleeves rolled up, jeans, black Kenneth Cole casual shoes.
I think I’m in love. 
I’ll throw in my sex & age…I’m F and 40. When I described my typical outfit above, I was thinking more about winter, since we are in the middle of a seemingly endless one right now. In the summer, I wear capris just about every day, and although some of my pairs are denim, I tend to get them in different colors & patterns, and I wear them with t-shirts or sometimes a lightweight sweater. Sometimes I’ll wear low-top Chucks with them, and sometimes I wear flip-flops or other sandals.
I’m interested to read that some folks still wear Docs…I still have a few pairs (even a b&w spectator pair, like Big Bad Voodoo Lou!), but never think to wear them anymore.
Cite.
I’m not *that * dedicated, but I did get married in a Hawaiian shirt…on the beach. Not in Hawaii, unfortunately.
You know, I think it’s a little sad that we all have an answer to this. I’m making a note to add some variety to the wardrobe next time I shop. But the answer for me is: solid, red, black, or blue T-shirt, preferably with a V-neck, long-sleeve in winter, or sweater, jeans or chinos, and comfy shoes that aren’t quite sneakers, like Sketchers.
I can dig up photos of my wedding. That one I can document. I also wore a Hawaiian shirt to my father’s memorial service a couple of years ago. That one I don’t have photos of.
Ramones tank top. I have some “official” ones, and some I made. Black jeans. Boots. Ankh.
Winter - Solid colour v-neck fitted sweater, tight boot-cuts, strappy heels.
Summer - short shorts, halter tops, flip-flops
Female, 27
I love my style.
Wow - honey, is that you? 
Take away the flip flops, replace them with workboots or a pair of AirWalks or Vans, and you pretty much have my fiancee’s entire wardrobe summed up in one sentence.
Hm. Mine too, now that I look down at my “Plunder Bunny” tee and denim capri’s. Oh, and my skull 'n crossbones flip-flops. 
Is this an Orlando thing?
Different styles of jeans, black belt, black, clingy shirt, and black shoes. In the summer, I wear capris, chinese shoes, and mostly black shirts, but I do throw in white shir s as well.