Halloween costume ideas for the well dressed guy

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.
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#1.  Secret Service Agent

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

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

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.