Margot Tenenbaum, The Royal Tenenbaums: Although the Chaz, Ari, and Uzi trio of Adidas tracksuits are always a Halloween hit, stone-faced wild child Margot's signature look is for sure the top Tenenbaum style. For the playwright prodigy's iconic ensemble, you'll need a full length fur coat, a striped Lacoste dress, a carton of American Spirit yellows, a pair of four-fingered gloves, a single Goody barrette, and eyeliner applied like you're applying for a job at the local Hot Topic--with the attitude to match. Margot's look is perfect for an afternoon of sneaking around with the brother you're secretly in love with, or a relaxing night in spent chain smoking in the bathtub while avoiding your husband.
Takako Chigusa, Battle Royale: Kinji Fukasaku's Japanese cult classic in which a class of 42 ninth-grade students are kidnapped and forced to fight to the death makes The Hunger Games look like an episode of Sesame Street. While the bloody school uniforms make for incredible costumes, class 3-B's baddest babe Takako Chigusa steals the sartorial show. If you've got a yellow tracksuit and know your way around a jackknife, this lethal 14-year-old is your best bet this Halloween.
Annie Hall, Annie Hall: Well la-di-da! Grab a glass of chocolate milk and break out Grammy Hall's hand-me-downs for a costume inspired by our favorite Woody Allen heroine. To achieve Annie's signature menswear-minded look, think slouchy trousers, crisp button downs, large ties, and lots of layers. Bonus points if you can belt "It Had to Be You" at karaoke and keep any rogue lobsters at bay.
Justice, Poetic Justice: Earlier this month, Janet Jackson returned to music with the blockbuster release of 11th studio album, Unbreakable -- her first in seven years. But Ms. Jackson also has a few film credits under her belt, including the lead role in 93's Maya Angelou-inspired love story Poetic Justice. Justice's wardrobe is a pretty easy fix for any last minute scrambles (if you already happen to have beautiful braids and the Jackson gene for bone structure). All you'll need is an oversized jersey, high waisted jeans (JJ loves some good mom denim, don't forget), and a page boy cap. Bonus points if you've got a feline companion like Justice's cat, White Boy, or are boo'd up with anyone who bears the slightest resemblance to Janet's co-star, TuPac.
Heathers, Heathers: The Plastics might have ruled North Shore, but Westerburg High School bowed to the original mean girls, the Heathers. Although Sherwood, Ohio isn't exactly a style capital, Heathers Duke, McNamara, and Chandler (plus one monocle-clad Winona Ryder as the homicidal Veronica Sawyer) kept it really very on the croquet court with bright blazers, pleated skirts, opaque tights, and shoulder pads for days. Top dog Chandler even marked her queen-bee status with a signature red scrunchie. So, what'll be your damage this Halloween?