Halloween is, after New Year’s Eve, the biggest party night of the year. While going out and getting hammered for its own sake is always in fashion, there’s a good chance you’re also trying to pick up. Halloween not only allows you to be a little more forward with women than you normally would be, it also lets you dress in a way that attracts a lot of attention. On All Hallow’s Eve, you don’t need a pickup line. All you need is a conversation-starting Halloween costume.


Max from Where the Wild Things Are

How To Do It: Wear footie pajamas. You can totally get them for adults. Fashion yourself some kind of crown and scepter and you’re ready to go.
What It Says: I’m not afraid of my inner child… he’s actually kind of a badass.
What She’ll Say:
“Ohmigawd! That was my favorite book when I was a little girl!”


Monster With Human Prisoner

How To Do It: Get a monster costume with a top that stands up on its own. Make a phony cage. This is where the upper part of your body goes. Get some fake legs and you’re good to go.
What It Says: I’m kind of weird, but good weird.
What She’ll Say:
“How’d you like to make me your prisoner?”


Michael Jackson

How To Do It: Dress like Michael Jackson. Extra points for being a zombie version. Monkey and medical mask optional.
What It Says: I’m funny in a cruel sort of way. 
What She’ll Say:
“That’s the scariest costume I’ve seen all night.”


Han Solo, the Carbonite Years

How To Do It: Get a very large box and wrap it and yourself in tinfoil while making the pose. Withdraw your arms. Cut out the entire face because tin foil on the face is no fun.
What It Says: I love Star Wars. I’m kind of a closet nerd.
What She’ll Say:
“I love Star Wars. I’m kind of a closet nerd.”


How To Do It: Wear nothing but shorts and shoes underneath a trench coat. Extra points for creepy sunglasses.
What It Says About You: I’m edgy and probably a little perverse.
What She’ll Say:
“What’s underneath your coat?”


Nudist On Strike

How To Do It: This is an updated version of the “I’m a serial killer. We look just like everyone else” idea. Just wear whatever you’d normally wear. Hold a sign that says “Nudists Union Local #94213 ON STRIKE.”
What It Says About You: You had a way creepier costume idea than this.
What She’ll Say:
“What do we need to do to end this labor dispute?


Mammogram Machine

How To Do It: Make a box around your head and shoulders with two curving cuts at the bottom for the boobs. Label it “FREE MAMMOGRAMS.” Is there a cheesier costume? Not that we know of.
What It Says About You: I’m a boob man and I don’t care who knows it.
What She’ll Say:
“Is this equipment approved by the AMA?”


Toilet Paper

How To Do It: Wrap your body in a circle of poster board. Have another piece sticking off tangentially (get out your high school geometry book, kids) for the loose part of the roll. This can also be done with old sheets.
What It Says: I’ve got a self-deprecating sense of humor.
What She’ll Say:
“I’ve got a job for you.”