When I go to things like preview receptions of art exhibits or backstage at local theatre, I go for something a little more flashy than normal. Maybe a British high-buttoning suit with a bowler hat. Or a serape as a cape. Or a vest cut from cloth with a Picasso motif.
Dirty Boxers and a “Who Farted” T-shirt with stains and a hole in the tail.
Might work for performance artists in the subway.
Anything that goes well with open-toe four inch red faux alligator heels.
I do the all-black “I’m an artist” look. As of now, I am still yet to convince anyone.
Washed out jeans, tan hiking boots, a white t-shirt and a navy blue double-breasted blazer worn open.
Quasi
Wait…I’m supposed to wear clothes? On the internet?!?
If I have to prove to someone that I’m a guy that they are to associate the term “Cafe Society” too, I generally just act arrogant. I don’t have to try hard.
Carharts…
feel the canvas, be the canvas.
Classic black tuxedo.
Red bow-tie and cumberbund before 7 p.m., black after.
Since I’m so into musical theatre, I wear my Eva Peron long white dress with the Madonna bullet bra on top, my Cat-in-the-Suessical hat and carry my Mamma Mia! beach ball.
I love looking cultured.
I wear a black, be-sequined Margaret Dumont evening gown and carry a lourgnette, in honor of Eve.
Yes, I know I’m a guy. Shut up.
Black Tux with turned down collars. Put it on the night before and sleep in it and wear it all the next day. Maybe play a pick game of baseball or basketball. Need to have that ‘lived in’ feel. Now I’m ready.
Oh, and a pint of Ripple in my back pocket. Need something to wash down those damned stuffed grapeleaves with.
carhartts has two t’s.
I do tend to wear black, too. I have a lot of black clothes so it’s not unusual for me to wear it anyway, but I gravitate towards it for artsy events.
I also tend to wear my funkier clothes and my funkier jewelry.
my maroon Doc Marten boots, my worn brown felt fedora, my black silk shirt with the re and gold dragons on it and a pait of black knee length carpenter shorts
Black Polo button-down, Levi 505’s, silk tie (Frank Loyd Wright inspired design -predominately dark green), cowboy boots (or Cole Hahn’s), black linnen calf-length duster and a (Jack Nicholson - ‘Witches of Eastwick’) ponytail.
You have now achieved goddess-like stature in my eyes.
Neither scruffy not artsy, I dress in black simply because that’s all I wear. If I plan to mingle with a classical crowd, I’ll wear a black button-down shirt with my black jeans–that’s my only concession. Otherwise, it will be a a neat tshirt, often featuring a Celtic or fantasy theme. I am topped by long, neatly brushed hair and stand upon feet shod in Faire boots of soft black leather, with dark green trim. Sometimes a bit of quiet silver jewelry will accompany the ensemble. In bitter cold, a trenchcoat may make an appearance.
In other words, I “look” like myself–neither fancy dress nor grunge suits me.
::hides head in shame:: I usually punk out. Well, somewhat. No piercings, but black jeans, usually a shirt that I’ve made. Obvious eyeliner I do interesting things with silver chains. Or else, I’ll go sort of earth tones, use a homemade headband, dark blue jeans, a white shirt with a brown cord. jacket.
Of course, I’m eighteen, so any fashion faux pas can be written off as immaturity.
The worst thing I ever did was for a fairly high profile ball/gala thing last January. Antique lace shirt, skirt that DID NOT match. I was going to wear a pair of nice jeans, but my roommate protested. A lot. I looked like crap, and I knew it. And CN-freaking-N was there.
Anyway…don’t do that. 
Jackets are my first and only love.
For artsy events I have two choices. The first is knee length grey wool double breasted coat, worn with a long black scarf, rhinestone jewelry and dark sunglasses. This jacket man, it is awesome. Looks like somethng out of a noir film, but it still manages to look elegent and not costumey. When I wear it out people look and point and say “That, my friend, is one hell of a jacket”.
Twelve bucks at a thrift store. Awesome.
My other nice jacket is a black satin padded chinese jacket, with a mandarin neckline and frog closures. Twenty bucks at a thrift store. It is an awesome thing, and the perfect antidote to my other padded chinese jacket- which is in flourescent pink and blue.
Other than that I will probably be wearing jeans, a tank top and sparkly hairclips.