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The Compass  /  Seasonal  /  Halloween Costume Ideas for Men of Style

Halloween Costume Ideas for Men of Style

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Remember when Halloween meant dressing up and putting on a paper mask that invariably malfunctioned two minutes into your trick-or-treating so you had to carry it around all night and you didn’t scare anyone?

Things have changed. You can still take the opportunity to don a costume and enjoy the annual fright night festivities, but you’re a grown man now. Your costume should reflect your maturity and, of course, your knowledge of style (good, bad and downright ugly style). What’s more, your Halloween getup ought to display some wit. Anybody can buy a mask or a ready-made costume but only the truly resourceful man can come up with a costume based on the items in his closet that’s fun and creative.

Here are three that fit the bill.

Nucky Thompson NUCKY THOMPSON

You don’t have to be “kinda funny looking” like Steve Buscemi to turn yourself into the corrupt politician/unscrupulous gangster protagonist of Boardwalk Empire. You just have to pay attention to detail. When it comes to dapper dons Nucky can go toe-to-toe with the best of them. With his penchant for patterns displayed in double-breasted and three-piece suits, Nucky epitomizes the 24-7 dressed-to-the-nines man of the 1920s.

Nail the look

  • Wear a patterned three-piece, like the Brownstone Brown Glen Plaid Custom Suit from Black Lapel. Don’t have a three-piece? Try a double-breasted. Don’t have a double-breasted either? Try a strong contrast windowpane.)
  • Put a huge blooming carnation in your lapel. (Not a medium or pretty big carnation, the trick to getting costumes right is pushing things to the extreme, so get the biggest most gargantuan carnation you can find and stick it in your lapel.)
  • Rock the old-timey details. Sport a pocket watch and a tie pin (two Nucky calling cards) and carry a flask full of moonshine (we like Dutch’s Spirits Sugar Wash Moonshine for authenticity purposes but you can swig Gatorade if you’re driving, that’s the beauty of a flask, nobody can see its contents).

Advice from the pros

Steve Buscemi on playing Nucky Thompson:

He’s a fun character to play, and to be in his shoes. In his very expensive shoes.

Buscemi’s got a point – if you’re going to be Nucky this Halloween, you’ve got to come correct with the footwear, son. And polish those bad boys before you step out.

Julian Assange

julian assange

The Wikileaks founder is the nothing if not controversial. Love him or hate him, there’s no arguing his nerdy style has improved drastically over the years. Still, one of the more iconic images of the man is one of him in a black and red shirt/tie combo (no wonder some people think he’s the devil incarnate) that only Dwight Schrute could love.

Nail the look

  • Wear a dark gray suit to further worsen your black shirt and bright red tie ensemble.
  • Get a white wig or, if you’re hardcore, you can dye your hair (we know you care about your mane, so try white hair powder from Bumble & bumble to keep from doing permanent damage).
  • When attending Halloween parties, carry around a ream of paper stamped “Top Secret” and continuously leave it “lying around.”

Advice from the pros

Benedict Cumberbatch on the costuming elements of playing Assange in The Fifth Estate:

I really quite enjoyed putting the wigs on.

Key takeaway, only famous actors can get away with playing with wigs except for one night a year, use it wisely.

Saul Goodman

SAUL GOODMAN

It’s hard to imagine anyone  stealing scenes from Bryan Cranston in Breaking Bad. It’s even harder to imagine somebody stealing scenes from Cranston with humor (Cranston cut his teeth getting laughs on sitcoms like Seinfeld, Malcolm in the Middle and The King of Queens). Actor Bob Odenkirk manages to pull it off, though, playing Saul Goodman. Hit up a Halloween shindig dressed like, and acting like, Saul and you’re likely to steal the scene as well. Part license to be a schmuck, part excuse to purge your closet of a really horrible shirt, this costume is all about being ostentatious.

Nail the look

  • Start with a really wide tie. Make sure it has a big geometric pattern and add a puffed pocket square that sticks too far out your pocket (just be sure it clashes with the tie).
  • The shirt is essential. When choosing a color, try to match any NFL home jersey color except for the Chicago Bears. Socks in the same color will go a long way too, though no one will see them since your pants should form giant puddles of fabric at your ankles due to the huge fit (see the next bullet).
  • Ideally you’ll borrow an old suit from a buddy who’s 15-20 pounds heavier and an inch or two taller than you to get a truly Goodman-esque fit. If you can’t do that, dig deep and pull out that old three-button number you’ve been holding on to for sentimental reasons and give it one last whirl before chucking it into the “donate” pile.

Advice from the pros

Bob Odenkirk on people laughing at Saul’s manner of dress:

He think he’s dressing good, man! He thinks he’s got style…he’s a little mystified if they’re laughing at him. Like, he would say to them, ‘What are you laughing at? These socks are pure silk! That yellow dye is illegal in America. I had to go far to get these.’

Lesson learned, to truly embody Saul, arm yourself with a backstory for every part of the look. The more extravagant, the better. Also, do all your shopping at McGill & McGill.

HONORABLE MENTIONS

We went through a number of options before whittling our costume ideas down to the top three. Though the following didn’t make the cut we thought we’d give you a taste of some the other costumes you can pull off with some simple of the clothes you probably have in your closet.

HONOURABLE MENTIONS

With these options you’ve got no excuse for going without a costume this year. How are you suiting up this Halloween? Leave us a comment below.

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3 thoughts on “Halloween Costume Ideas for Men of Style”

  1. I will be going as Barney Stinson, Duck Tie and All!

    1. Black Lapel says:

      Awesome. That sounds legen….

      Wait for it!

      1. Black Lapel says:

        …dary! 😉

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