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Halloween costume ideas for the well dressed guy

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Almost all good Halloween costumes have a noticeable ridiculous factor.  Which is why going as James Bond doesn’t really work.  Yet at the same time, you don’t need to go full Sponge Bob Square Pants either.  There is an inbetween where those with an appreciation for style can be in costume, a little ridiculous, but still look good.  Half a dozen examples are below, with futher suggestions from you guys in the comments.  Top Photo: Doug Bowman
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#1.  Secret Service Agent
Limo or dark SUV = bonus points.

You’ll need:  Dark suit, white shirt, conservative tie, wire frame sunglasses, earbud, lack of shyness.

Incredibly easy, as long as you’re willing to stay observant and make other people a part of your costume throughout the evening.  Say little.  Talk into your wrist every now and then.  Converse with a prostitute.  The most important thing is to provide “protection” to anyone who’s in a political or royal costume.  When P90X Paul Ryan walks into the bar, make sure “Bowhunter” can do his crunches without obtrusion.  Somebody in a Nixon mask makes an appearance at the house party?  Get between him and any threatening monsters.  If Eastwood and his Chair struts in, it’s your job to make sure that “chair” goes unharmed.  It is after-all, the leader of the free chair world.

 

#2.  Seat Filler
Plus you’ll get a great lower body workout.

You’ll need:  A tuxedo.

For the guys who are lucky enough to own a tuxedo.  These are the people at awards shows who slip into a celebrity’s seat when they get up to use the bathroom so it doesn’t look like the audience is peppered with no-shows.  Once they return, the seatfiller stands up and retreats, waiting for the next seat to open up.  And yes, you can try and sign up to be a real one.  For Halloween:  Put on your tux.  Stick a “Hello My Name is: Seat Filler” nametag to your lapel.  Whenever someone gets out of a chair at the party, sit down in it until they return.  Try not to offer anyone turkey jerky.

 

#3.  The Most Interesting Man in the World

You’ll need:  A tux or dark suit, white shirt with the top couple of buttons undone, pocket square, grey beard/hair, Dos Equis, gaggle of beautiful women.

You might have to wear a wig & beard, or take a chance with some spray in color, but surrounding yourself with beautiful women, spinning incredible yarns, and drinking Dos Equis all night… well there are worse ways to spend an evening.

 

#4.  PSY in Gangnam Style

You’ll need:  Sunglasses, black pants, white shirt, black bow tie, light blue blazer, black gaffer tape, spectator shoes (optional) moves (not optional).

Head to the thrift store and try to find a light blue blazer.  There’s probably going to be some awful polyester thing there.  Use the black gaffer tape around the lapels and other edges on the jacket.  Careful if you’re doing this on a blazer you already own and like, the tape might leave a residue.  Don’t get too hung up on the white & black spectator shoes.  Do get hung up on the dance moves.  If you don’t have those, you shouldn’t be doing this.  With half a BILLION youtube views, PSY is going to be everywhere this Halloween.  And plenty of them will be able to dance.

 

#5.  Indiana Jones:  Frye Walter – $208.60 ($298) | Indiana Jones Fedora – $28.80
Remember. Snakes. You hate snakes.

You’ll need: The hat, brown boots, medium khaki chinos, an off white shirt, leather jacket, whip

What an outstanding excuse to get yourself the Frye Walter, which looks a hell of a lot like the $480 Alden 405.  The Frye’s are less than half the price of the Aldens thanks to a sale at Bloomingdale’s.  And these Frye’s are no slouch either.  They’re made in the USA from full grain leather and ride a goodyear welt.  And then there’s Kohl’s, who sells the official Indiana Jones fedora for under thirty bucks.  That’ll do.  The pants should be easy since they’re a basic medium khaki, olive, or light brown chino.  Add a safari type of shirt and you’re set (the new jcp white OCBD would be fine in a pinch).  Hit your local thrift store for an old leather or leather-like jacket if you want.  Add a brown messenger bag if you’ve got one.  The bull whip:  Five bucks through Amazon.  Sure.

 

#6.  George Valentin from The Artist

You’ll need:  A suit with some classic appeal, slicked back hair, pencil thin mustache, Jack Russell Terrier (optional), the ability to keep quiet for an evening.

Perfect for the introverts.  You do not need a tux with tails to do this.  Any suit with some sort of throwback appeal (wider lapels, a three piece, etc…) will do.  Slick your hair back.  Shave or draw in a pencil thin mustache.  Don’t speak.  Exaggerate your facial expressions instead.

Got a great idea for a costume for this year?  Have one that worked particularly well in the past?  Leave it below.

Comments

  4. I say go all out and Not be the guy in a suit as usual. It’s the only acceptable time to dress as a ninja, dinosaur, or woman (unless you’re into that). Being out of character is awesome

  6. I want to be Indiana Jones for those boots. And for an excuse to wear a fedora for the night.

  7. I’m doing the US Olympic Team outfit – very light stone slacks, white bucks, white shirt, blue and red repp tie, blue blazer with a phony felt polo logo, and I ordered the silly beret from the Ralph Lauren site for $14.99, free shipping. Thinking of adding a fake grill to be Ryan Lochte, or carrying a bong around ala Michael Phelps.

  10. Best dressed is Clark Kent.

    Go to the op shop and buy a cheap shirt. Cut the buttons off, glue them to the outside and line it with Velcro. Wear a superman shirt underneath.

    Wear your best suit on top.

    Tear open at every opportunity.

  12. BTW, take an additional 15% off those boots if you open a Bloomingdale’s account, sizes are going quick though. Excellent customer service, gave them a call and they’re actually shipping mine from a store rather than their online warehouse which already ran out of my size.

  15. I’ll be going as Tony Stark. It’s going to be close to the picute below. and yes, I made a repulsor gauntlet

  18. Absolutely. There’s no intent here to discourage those that want to go all out. But if you’re not the type to do so, and/or need something quick and easy to execute, these are somewhere inbetween.

  19. I nominate Jeff Winger’s David Beckham from Community. Slim grey suit, tieless, top 2-3 buttons undone, coiffed hair, soccer ball.

  20. Barney Stinson is another easy one, just say “It’s gonna be legen—wait for it—dary! Legendary!” all night and you’re golden.

    Find the duck tie and you win.

  21. We’ve already got our halloween costumes. Our whole family is coordinated, and by “whole family”, I mean me, my wife, and our dog. They’re both going as bees and I’m a beekeeper.
    I wanted to go as Psy, but my Korean sister-in-law says that only works for Asians. I also wanted to go as Big Tex (the Texas State Fair attraction that burned down), but official replica shirts were $60! 😛

  22. If this article was written in the early 00’s, I would suggest Bill Lumbergh. I can only imagine that well-dressed men looked like him in that time period.

  24. Halloween is the one day where being dapper is not only unnecessary, but potentially very lame as well. Secret service agent? Yea that will go over well…

  29. Heisenberg.

    Chinos, black porkpie hat, black sunglasses, black jacket, tattersall dress shirt, white undershirt. Blue rock candy is what they use in Breaking Bad for the blue meth props. I’ve got a couple pound bag of crushed up rock candy, plus a .38 snub nose water pistol.

  34. My 2nd best costume to day (next to when I was Kid Rock) was when I was Paris Hilton and my gf was Nicole Richie. Yes, it was as weird as it sounds

  35. Inspector Gadget would be an awesome one, too… pretty basic attire there and you can get creative with one of his ‘gadgets’…. but not too creative where you end up in jail or injuring yourself/someone else.

  37. I’ve done the Clark Kent thing before. If I was smart I would have just used a Superman t-shirt. Instead, I used a molded muscle chest piece. It was too billowy so I cut out all the flimsy cloth straps and strapped it on using small bungie cables. It dug into my skin and hurt like hell. I won the company costume contest, but I’m still not sure it was worth it.

  38. Already wear the glasses and love my 3 piece thrift pickup, just had to gel/curl the hair and throw on my old superman shirt. Bow tie because that’s what what I wear every day to work.
    [IMG]http://i49.tinypic.com/351sp6h.jpg[/IMG]

  39. Going to a heros & villains-themed party with my lady. We will be Bonnie and Clyde. We considered going as post-shoot-out versions, bust I think we’re going to be in full health.

  41. I thought this was going to be a silly article, but it might just be the best thing on dappered this week(and this has been an awesome week)! Loving the inidiana Jones idea…might be the best excuse I’ve heard to splurge on the Alden’s I’ve been eyeing

  43. Just search up the Dappered steal the style! The white jacket could be difficult though…. maybe sub it for the cool white one Gosling wears in Crazy Stupid Love one time.

  44. My personal best was Jules (and my buddy was Vincent Vega) from Pulp Fiction. I also dressed up as Tyrone Biggums before which went well in Columbus, OH but not well in Baltimore, MD. And William Wallace was also a valiant failure. I love Halloween, good ideas here!

  46. I will be dressing up with a couple of college buds as the Avengers. Since I have long hair- I will be Thor. Black cargo pants and boots, long sleeved “armor”, cape, and of course, muscle suit underneath

  49. I can’t believe no one’s mentioned one of the top costumes of this year, 50 shades of Grey, Christian Grey…Basically you can wear any suit and/or shoes you want with a silver tie…Then one piece bondage, if you don’t already own a pair of handcuffs, supermarkets and drug stores carry the kids one for $5-$10…You can attach it anywhere…Around your tie, on your wrist, attach one end through the bottom button hole on your jacket. You could also look into get other pieces of bondage or a masquerade mask…

  51. You can be funny and dress up as a stereotypical nerd, penny loafers, short sleeve oxford with a tie and readers

  55. I went as Napoleon last year: i put on a blue trench with off-white khakis and black rain boots. then i made a ton of epaulletts, medals, and a black hat out of felt and waved a saber around all night spewing “ALLEZ-Y!”

  56. I went to a Halloween party last night that I had no intention of going to. Threw on my slacks and a buton shirt, combed my hair and claimed to be dressed as a responsible adult (college. yeah.)
    By the end of the night it had changed to “I’m yo daddy” to the ladytypes. (see again: college. yeah.)

  57. My girlfriend and I went as PSY and one of the girls from the video. We won best group/duo costume. Op op op op oppan gangnam style!

  58. I say go as a dick. Just walk around naked and shake your junk at people. Girls really like that 🙂