Cecilia Rebecca Ziko: One year my brother's friend dressed up as The Best Man: disheveled and in an ill-fitted suit, top buttons and tie undone, shirt half untucked. Maybe missing a shoe. He spent the night standing on chairs making toasts, spilling his gin and tonics, putting his arm around people and telling them awkward stories. Doing the worm. Whenever someone asked who he was suppose to be, he would act all offended, "What do you mean 'Who am I?' I'm the best man!" I think he ended the night passed out in a closet.
Drew Zandonella-Stannard: One of my old coworkers once went as a garden gnome. She basically just dressed herself as a gnome (very comfortable and warm) and carried around a plot of fake grass that she would stand on from time to time. Sort of brilliant! This could easily be reinterpreted as a "sexy" garden gnome, but really, who can beat wearing a cozy drinking suit AND having a clean place to plop yourself down?
Jane Marie: The best one I ever saw was on a stranger BUT all my friends were with me so it would be lame for me to copy it. Here's what it was: a door guy. He was a dude dressed up like a regular juicebox wearing sunglasses, and he had a velvet rope, complete with the metal stand thing (where did he get one?) and a clipboard. The best part was that he never broke character and he was such a jerk and kept stationing himself in busy places like in front of the bathroom door. Luckily, his "guest list" had every single "sexy" costume on it: Sexy Nurse, Sexy Vampire, Sexy Zombie. I was Suri Cruise that year so I got in to the bathroom as "Sexy Baby."
Jaya Saxena: There was a girl in an engineering school that went as "Sexy Transistor" and wore a nude bodysuit with this design all over it.
Helen Rosner: My all-time favorite was worn by a UChicago grad student (of course). He had on a t-shirt with a silhouette of the continent of Asia on it, and was wearing one of those forehead flashlights. Get it? ASIA MINOR.
Marie Lodi: Mormon kid on a bike — white button up shirt, bike helmet, backpack and name tags.
Lili Loofbourow: The God of Small Things sported a toga made of a sheet with lots of tiny items pinned onto it: tiny scissors, miniature saw, buttons, etc. Princess Leia hair topped by a crown of laurels.
Bianca Turetsky: My friend Kristen has been trying unsuccessfully since college to get a Donner Party together. Everyone in the group would be wearing ripped and dirty pioneer-style clothing. Some people would be missing limbs and maybe someone would carry a heart on a stick or be eating ribs.
Abe Sauer: My favorite, that I attempted last year but ran out of time, is perfect if you have babies. Dress yourself (dad) up like the Empire State Building. Tall hat with Empire State Building characteristic top. Cardboard flat sides with windows on them (open a few and hang Barbie dolls out for extra awesomeness). Baby dressed as a gorilla (suits are available for this) hangs on the front of the the dad dressed as Empire State Building, as King Kong. Baby King Kong also holds blonde Barbie (obvs). On top of hat, use hard wire to make two or three biplanes circling. Extra credit: Other child (old enough to walk) is dressed as one of the biplanes. Kind of like this, but with an old biplane look to it. That child then runs around the Empire State Building and King Kong. HIGH CONCEPT!
Molly Shalgos: The best one I ever saw was the one my babysitter wore to take me to a costume party in third grade. Not sexy, not sultry, 100% awesome — she came as a gumball machine. Red leggings, red turtleneck, and a little red pillbox hat, and she'd cut arm holes into a huge, clear plastic bag. She tied off the bottom of the bag, and then filled it up with tiny multicolored balloons, and taped a cardboard 25c sign on the front of the bag. The pictures still crack me up.
Erin Sullivan: I’m aways a fan of a conceptual costume, and one of my favorites was A Lightening Victim, where a girl teased the S out of her hair, smeared dirt all over her body, and charred her clothes.
Lisa Richey: The Morton salt girl.
Allie Pape: A was a guy wearing a T-shirt that said "Go Ceilings!", a hat with a big C (might have been a Cubs cap), and a big foam finger with "#1” on it. What was he? A ceiling fan!
Danielle Roderick: The best I've ever seen was "the woman who wants your slot machine." This was a couple of years ago, so she had a big plastic cup full of quarters, some NICE Oscar de la Rentas, and a thriftstore warm up suit, complete with fanny pack and cigs. It was fun because she got to wear major makeup (big lips, mascara city, fake wrinkles), and another dude had dressed up as her husband, who was always circulating the party looking for his crazy wife, who said she was going to the penny slots, but now he can't find her. He had on suspenders, faux belly, and was smoking a cigar. They would shout at each other across the party to shut up, and to meet at the buffet.
Kathleen Walsh: Sexy Gorilla (gorilla suit with bikini on top, high heels).
Katie Heaney: My friend and his group of friends once went as The Baldwins and basically all wore leather jackets and then made duck lips/Blue Steel faces in every picture.
Megan Dietz: Unladybug. Ladybug costume plus cigarettes, ripped stockings, and a bad attitude.
Josh Duboff: A few years back, my friends and I for some reason decided to go to the Halloween parade in Chelsea. On our way back to our friend's apartment afterwards, a beautiful man dressed in a tuxedo (a red rose in his lapel!) biked in front of us. He was holding a white sign that had "I'm sorry" written on it. We all shouted some variation of "What are you?!!" at him at the same time. "I'm... a formal apology," he responded, and we all swooned as he biked off into the distance.
Megan Collins: My favorite — and maybe this has been done, but I thought it was clever? — was a guy dressed up as a kissing booth. I have no idea how he rigged it up, it was kind of like a cigarette girl thing, where there was a strap across his neck and then the flat surface in front of him, but it extended up on both sides and connected at the top where the sign was.
Edith Zimmerman: A sexy lamp. Gold bodysuit, lampshade on her head, tassel coming down from her ear or somewhere. Amazing.
Arianna Stern: A few years back, my brother dressed up as grapes. He stuck a safety pin through the stubby knot-end part of inflated, purple balloons, and attached them to an all-brown outfit. The nice thing about this dirt-cheap getup is that it's able to accommodate hot or cold weather. Beware, though: In a tell-all email, my brother wrote, "People kept running up to me throughout the night and trying to pop them or pull them off. By the end of the night I was literally pushing away drunk strangers."
Nozlee Samadzadeh: The best costume I've ever seen was Miss America in a Parade: the girl in question wore a leotard that she'd bedazzled to look like the top of an evening gown, a sash with MISS AMERICA 2006 written on it, elbow-length white gloves, nude pantyhose, and gratuitous heels. Her hair was upswept, hairsprayed, and tiara'd and she wore a ridiculous amount of makeup. And...there was a tiny papier-mâché red convertible hanging around her waist, with a clear windshield, little doors painted on, working headlights, and everything! She spent the entire night smiling really big and waving with her white-gloved hands.