If you were trying to go as The Wintour but couldn't rope anybody into being Andre Leon Talley, just go as The September Issue itself. Dress in black and tape magazine pages all over your clothes—with the September Vogue cover front and center.
Want an excuse to be funny-slutty? Good thing American Apparel is as common as Starbucks these days. Buy a flesh-toned bodysuit and a jumbo black Sharpie, contour your lumps 'n' bumps, and make yourself into a Topographic Map.
Most of us are familiar with the Mac Spinning Wheel of Death. The terrifying orb that bodes hard drive failure and an imminent reboot is also an easy costume—just throw on a light blue sweat suit, track down a rainbow umbrella, and spin it in front of you all night. Alternately, print out a giant SWOD icon on a couple sheets of paper and tape them to yourself. Grim Reaper mask and scythe optional.
We're not necessarily big gun fans, but going as The Second Amendment will give you the right to bear arms. Two options: Find some fake fur and attach OR find two stuffed bears, cut holes in the bottom, and stick your arms through them.
For a get-up that's functional—and by functional we mean dispenses alcohol—go as Boxed Wine. Buy a box of Franzia, scan the label, print out a jumbo version, and paste it on both sides of a large, human-ready box. The best part: Duct tape the bag of vino to the inside of the costume (with a hole made for the dispenser, of course.)
Don a pretty, lacy slip, a fake beard (cotton balls are fine), and round, wire-rim glasses. You'll be inspiring Freudian Slips while dressed as one! Punny.
And finally—If you decide this costume thing isn't your cup of cider, take a white box and use a black Sharpie to write IT in large letters across the top. Now you can be With It and tell others to Get With It. You can be an It Girl. And put It under your chair, or straddle It, to show your disdain for the whole affair. Yup, you guessed it: You're Over It.
See Last Year's Guide to Quick Easy Halloween Costumes.