• Anna Wintour: To recreate this Halloween's classic look you will need a medium-blonde bob wig with blonde highlights, dark face-eating sunglasses, a fur coat thrown over your shoulders, a requisite copy of Vogue, and an icy demeanor. (We recommend hanging out at a DMV or your local traffic court for a few hours prior to getting into character.) The look is ideally accompanied by a friend in a Karl Lagerfeld costume, but you can come together with a submissive latté-carrying assistant whom you'll use throughout the evening for target practice when chucking your Hermès Birkin bag.
• The American Apparel Girl: Yet another way to look ingeniously slutty for Halloween. You will need a pair of golden lamé hot shorts, legwarmers or knee-high socks and, of course, a unitard. The look is perfectly accented by a headband, compulsive popping of bubble gum, and occasional nip-slip. (Hint: American Apparel costume items are 15 percent off right now.)
• Jeffrey Sebelia from Project Runway: This is an easy look to pull off—you can use eyeliner for the neck tattoo, a pair of black jeans cut off at the calf, embellished and rimless sunglasses, and a tight, striped shirt. For this costume you should use any opportunity to be rude to someone's mother. To make it really memorable you can carry a Tim Gunn blow-up doll that can also double as Michael Kors. NY Mag has its version of the Jeffrey getup, too.
• Stylist to the Stars Rachel Zoe: You will need a color-clashing Pucci dress (if you don't have one handy, any colorful paisley gown will do), large gold bangles, rings, a python Fendi bag, and huge glasses on top of your head. The trick here is the unnaturally dark orange tan and deep forehead wrinkles that you can easily paint on with some eyeliner. To really get your point across you will need a large round badge reading "I made Nicole Richie Anorexic—Ask me how."
Photo: PatrickMcMullan.com