How do pirates dress for Halloween? They can't strap on a peg leg, prop a plastic parrot on their shoulders, apply an eye patch and wrap a red bandana around their scurvy heads. That's no fun at all -- not for a pirate on Halloween. That would be like we landlubbers wearing a suit to a Halloween bash -- the same suit and "business casual" clothing that we wear to work each day.

I happen to know how pirates dress for Halloween. I know it because I am on intimate terms with pirates, or as intimate as it is possible to get with pirates, as I always have to watch my back for the odd blade or misplaced cutlass. I even once sat in on a pirate support group as part of my research into all matters piratical, and made a good many friends that evening, although they were not lasting ones, the members of the group mutinying in the church parking lot and puncturing the tires of their rivals. (This caused hard feelings and the pirates consequently disbanded the group.)

Pirates, and this is important, do not dress like swashbucklers on Halloween. Pirates are, among their other attributes, consummate non-conformists. How can they dress like pirates on Halloween when everyone else dresses like them?

Halloween is a sacred holiday in America, and that is primarily because more liquor is sold on Halloween than on any other holiday. This particular holiday, therefore, is quite important to buccaneers. Far be it from them to let it be taken away by landlubbers.

I am surprised that more liquor is sold on this holiday than on any other holiday. There is the Fourth of July backyard barbecue, when we look up to the sky to see the rockets' red glare with a beer in our hand. Let's not forget the Labor Day picnic, when so many drown their end of summer sorrows with frosty drafts. Thanksgiving is good for a couple of glasses of Merlot, which goes well with turkey and cousins that you cannot otherwise stand the rest of the year. Christmas means extra cheer in the guise of spiced wine and aged whisky. Bubbly is for New Year's Eve and Mimosas are for New Year's Day. You have not lived, or regretted it, until you had your fill of Mogen David wine at a Passover Seder. Memorial Day, I believe, is a weak sister of a holiday when it comes to imbibing alcohol. No one is in a party mood on Memorial Day because they know that they have to go to work the next day, and no one except the most extreme radical liberals from Harvard or the entire state of California enjoys seeing John Wayne get shot for umpteenth time in "The Sands Of Iwo Jima".

Understand that the true pirate does not conform to norms of behavior, and so if everyone else is getting smashed on Halloween, the true pirate must remain sober. As nonconformity is a pirate's calling card, there is no better way to dis the rest of the populace than by staying stinking sober.

Everyone else grabs candy or plays pranks on Halloween. What yucks are there in that for a pirate that takes whatever it wants, and engages in antisocial behavior all year long? Sea dogs, consequently, not only observe the law on Halloween but also are stalwart citizens. They even help old ladies cross the street, and not into oncoming traffic, which is what they like to do during other days of the year.

Cutthroats are appalled at all of the faux pirates on Halloween.

Pirates must do the unexpected. Consequently, on Halloween, pirates dress as civilians. They dress like us while we dress like them.

Pirates wear pantyhose on Halloween. They keep their pantyhose scattered throughout the city and countryside, hidden away under the floorboards of laundromats and in little plastic bags behind the trunks of specially marked trees. Others wear leisure suits straight out of the Seventies, the better to mock us. (I hear from my sources that pooka beads and Qianna shirts are especially in with pirates this year.) They carry briefcases and wear neckties, and come to parties as insurance salesmen. A laptop bag or backpack, preferably embellished with a company logo, is always a tasteful accessory on Halloween. Cufflinks, among some old salts, are de rigueur and are always accompanied by a starched white shirt -- Brooks Brothers of course.

Now you know. When you see a proper gentleman or gentlewoman walking on your street this Halloween night, beware. You have just come face to face with terror itself, the embodiment of evil, not to mention a near perfect clone of us on every other day of the year. Aarrgghhh.

©2008 Edward Chupack

Author's Bio: 

Edward Chupack is an attorney for a major law firm. He lives near Chicago. His first novel, Silver, is available now from Thomas Dunne Books. To learn more about Long John Silver, please visit