Hipster grifter
Why: Kari Ferrell—a 22-year-old hipster from Utah who lied her way through Brooklyn, pretending to have cancer, lying her way into a job at Vice, and coming on to anyone with a Y chromosome—eventually ended up in jail in Salt Lake City. Although this costume will appeal to a limited Gawker-reading set, many haven’t forgotten this young lady’s antics, especially since her tale was used in a ripped-from-the-headlines Law & Order episode plot.
How: Get a hip haircut—a pixie or a bob with straight-across bangs will work—or buy a wig; try the Black Pixie Girl Wig at Ricky’s (various locations throughout the city; rickysnyc.com). Next you need a fake chest tattoo, easily done with a pen and a mirror (or ask a steady-handed friend—or get a temporary sticker). Ferrell’s tat was a phoenix, but a bald eagle could work too. Then add a low-cut shirt (the better to show off your ink), and a vintage skirt, skinny jeans or leggings. Make sure to carry a notepad and writing implement so you can pen things like “I want to give you a hand job with my mouth,” and “I want you to throw a hot dog down my hall,” two notes Ferrell wrote to unsuspecting Williamsburg residents.
David Letterman
Why: Haven’t you heard? The guy apparently slept around or something. Everyone loves a scandal, so you won’t have people asking you everyone’s most dreaded Halloween question: “Who are you supposed to be?”
How: You need thinning curls, gapped front teeth and wire-rim glasses. Grab some black lipstick to ink out a bit of your center chompers—try Trash and Vaudeville (4 St. Marks Pl No. 4 between Second and Third Aves, 212-982-3590) or your local Duane Reade, and while you’re at the latter, scope out the reading-glasses rack—write WORLDWIDE across your bum (to remind revelers of his company, Worldwide Pants), and top it off with a Late Show hat, available at the show’s website. You’ll need a suit and a colorful tie; if you own neither, check Salvation Army (various locations throughout the city; salvationarmyusa.org); if you want something more fitted, head to a wallet-friendly retailer like H&M.
Don and Betty Draper
Why: Because everyone you know is raving about Mad Men, the show’s won more awards than you can count, and you may be able to use clothes you already own.
How: To play the role of Don Draper—an austere, patriarchal, womanizing and altogether typical American man of the 1960s—you’ve gotta dress sharp, and that means a well-fitting suit and a skinny tie. Once again, Salvation Army and H&M are your best bets for cheap duds, or go for quality at Bloomingdale’s, Freemans Sporting Club (8 Rivington St between Bowery and Chrystie St; 212-673-3209, freemanssportingclub.com) or bespoke men’s boutique Elsa (217 E 3rd St between Aves B and C, 917-882-7395); the latter is also a bar. Don’t forget a crisp shirt, jaunty hat, shiny shoes and a pack of Lucky Strikes.
You don’t need naturally perfectly coiffed blond hair to play ’60s housewife Betty; that’s where Spirit Halloween Superstore (20 E 4th St at Lafayette St, 212-253-5705), New York Costumes (104 Fourth Ave at 11th St; 212-673-4546, newyorkcostumes.com) and Masquerade Times Square (311 W 43rd St between Eighth and Ninth Aves; 212-247-0104, masqueradecostumenyc.com) come into play. Try thrift stores for Betty’s floral dresses, pearls, and pumps. Before you trick-or-treat, take our Mad Men walk to really get into Don’s character and you’ll be sufficiently pregamed in no time.
Captain Chesley “Sully” Sullenberger
Why: The man saved 155 people by preventing a crash landing in the Hudson River—of course he deserves to be emulated in costume.
How: Once again you’ll need a suit—good thing there are so many out-of-work financiers to donate them to the Salvation Army—and this time it’ll be navy blue. Brass buttons, cuff stripes and a wing pin are all necessary. Make the cuff stripes out of strips of silver fabric or use some duct tape, and hit eBay for the wings (most costume shops only sell them with the full captain’s outfit). Don’t forget a white button-down, a navy tie, a captain’s hat and a trademark mustache; you can find the latter two at any costume store. Then, importantly, act heroic and trustworthy for the entire night.
Jon and Kate Gosselin from Jon and Kate Plus 8
Why: Jon and Kate Gosselin exemplify the contemporary American Dream: Fall in love, start a family, become rich and famous, cheat on each other, fall into a vicious legal battle and wind up on supermarket tabloid covers. Jon’s Upper West Side pad in luxury building the Alexandria, not to mention his chutzpah, make him somewhat of a New Yorker.
How: For Jon, throw on a short-sleeved white button-down one or two sizes too big, spike up your hair, and add a little forehead acne and some wraparound sunglasses. To make the pimples, you’ll need a little bottle of glue and a red Sharpie. Squeeze a few drops of glue onto wax paper, let them dry and roll them into zit shapes, then color them in and stick them on your forehead (be careful with the glue, crafters). Kate favors practical tops and denim, though surprisingly, not mom-jeans; for her hair you’ll either need a short hairstyle and a little pomade or a wig. Glue, sew, or pin eight baby dolls—cheap at Kmart or Target—on to your bodies to represent the poor mini Gosselins.
Lady Gaga
Why: Girl’s a badass New York native. She’s got a fashion sense all her own—pleather, plastic and origami are staples of her wardrobe—but we suggest going with the bubble outfit she wore on the cover of a June 2009 issue of Rolling Stone.
How: The last day of October will likely be a bit too cold to be naked, so get a flesh-colored body stocking at Ricky’s. White balloons from Party City (38 W 14th St between Fifth and Sixth Aves; 212-271-7310, partycity.com) work as bubbles; glue or pin them on. The blond Afro effect can be achieved either with a wig or some hard work in the bathroom with a comb or brush, a blow dryer, and a can of Aqua Net. Cover your mouth to keep out the fumes, and don’t forget magenta lipstick, mascara and faint purple eye shadow.
Plaxico Burress
Why: Plax made headlines in November of 2008 when he accidentally shot himself in the thigh at a nightclub. The gun was illegal, and last month the former Giants wide receiver was sentenced to a two-year prison term.
How: Although Plax was in evening wear at the time of the incident, dozens of media outlets reported (and mocked) the false rumor that he was wearing sweats at the time. So go with a nice loose pair with a Giants sweatshirt or some athletic shorts with leggings. Next you’ll need a short black beard and mustache, which you can pick up at a costume shop, and clip-on diamond earrings. What’s key will be the water gun in your waistband—get it from Target or Kmart—the blood dripping down your leg and the pained look on your face.
Bernie Madoff
Why: Madoff swindled investors—including a few celebrities, which is really beyond the pale—out of an estimated $65 billion. He was sentenced this summer and is currently serving a 150-year sentence.
How: You can either go with a traditional suit, and accessorize with burlap sacks emblazoned with giant dollar signs signs (try filling them with crumpled paper), or you can wear an orange prison jumpsuit; unless you plan to actually do time in Rikers before the 31st, you can get yours at Spirit Halloween Superstore. Naturally, the look is not complete without a Madoff mask, also available at Spirit. Raise the photoworthy factor by getting a bunch of your friends to follow you bearing torches and handfuls of overdue bills.
Dorota Kishlovsky (the maid from Gossip Girl)
Why: If you’ve seen the CW’s Web series Chasing Dorota, then you know that the Waldorf’s maid is actually a Polish countess with a secret ex-husband, Stranislaw, and she’s now dating a Russian doorman. Despite limited screen time on Gossip Girl, she’s the best character on the show.
How: Pleasantly plump Dorota is always perfectly groomed and most frequently seen in her maid’s uniform, which can be purchased at any costume shop. If you’re on the thinner side, pack yourself with pillows, down comforters, etc.—as a bonus, you’ll stay warm. If you want to dress it up further, Dorota looks ravishing in her red swing coat with the fur collar. Make sure to speak in an Eastern European accent, address everyone as “Miss” or “Mister,” and prominently carry a cell phone; Dorota’s always on call.
Mayor Bloomberg
Why: Mayor Mike may very well get to keep his title for another term, so he may be with us forever.
How: Anyone who’s seen a photo of Bloomberg in his casual wear knows that the mayor is no fashion trendsetter. Forgo the suit for this one, put baby powder in your hair, and don dark loafers, white socks, pleated khaki shorts, a white collared shirt and an American flag crewneck sweater. Don’t let anyone kick you out of any bar or party; change the rules if necessary.