Halloween is the only time of year when people can wear the most ridiculous outfit, gobble up twelve pounds of candy in one sitting, and act like a wild hellion (usually without repercussion) in the workplace. If you work at a company that doesn’t allow Halloween costumes, then you have two options.

You can either quit your job and find an employer that will let you channel your inner Halloween spirit.


You can dress up in a costume that lets you blend in with your workplace surroundings. That way you can have your own secret party while all of your coworkers continue to frown and work as if it’s just another normal day. Because of this helpful list, you can easily transport yourself from office to costume shindig without missing a beat or raiding a Party City.

Trust us, this trick will work. We haven’t tested all of these out yet but please feel free to do so yourself – as long as you give us all the credit!

Note: Any of these Halloween costumes – though masculine some of them may seem – can easily be worn by a woman.

1. Steve Jobs 


Yes, the late and ever iconic creator of Apple offers you a great place to start. This man was the king of simplicity – in tech and in fashion alike. His look is an easy one to pull off.

What you’ll need:

  • A black, slightly over-sized cotton turtleneck
  • Baggy, blue jeans that only unflatter
  • A pair of tiny, thin-rimmed eyeglasses
  • A bit of scruff or 5 o’clock shadow about the face (if you are able)

Tuck the turtleneck into the jeans. Leave enough room to make it look as though your shirt is a ship’s sail, catching hot air or hiding a midnight snack in its creases.

If you work in a high-tech office, this costume may win you adoration without anyone realizing why. If you work in any other sort of industry, this costume may give a new meaning to workplace solace. It all depends on how you sell it.


2. Coffee Stain


We are a nation of coffee drinkers so this one is a piece of crumb cake! Especially if you spent any time in the 70’s…

What You’ll Need:

  • Brown, beige, or black clothing – depending on how you like your coffee
  • Brown, beige, or black shoes
  • A bitter or artificially sweet disposition would add a bit of depth – depending, once again on how you take your coffee

Wear all of these things at the same time. To get into character, remain in the same spot for most of the day. Coffee stains rarely get up and move about. No matter how pressing an issue may be.

3. A Blogger


According to stock photos on the internet, a blogger is usually someone who’s attractive, hangs out in woody cafes, ponders often, and never ever plugs in their laptop. (We have reason to believe that their computers run on cold fusion, and that just isn’t fair.)

Real-life bloggers come in two basic forms: freelance and full-time. Each form has its own very different style of fashion. Use this (stock photo inspired) list to turn yourself into a full-time blogger.

What You’ll Need (Choose at least 3):

  • Thick-rimmed glasses
  • Form-fitting slacks
  • A lightweight scarf, draped around your neck loosely
  • Loafers
  • Suspenders
  • Bangs
  • A content and relaxed demeaner
  • A latte with its own special latte art
  • A vintage timepiece

Dressing as a Freelance Blogger isn’t recommended if you work someplace with strict dress codes or a disdain for laziness. If those things don’t apply to you or your workplace then all you have to do is put on a pair of sweats, ditch work, and head to the nearest cafe instead.


4. Almost Any Character From Mad Men (and From Any Season)


Is there a better way to trick your boss into liking you than showing up to work in a snazzy suit or pencil skirt? So unexpected and oh so chic! Your coworkers may think you’re trying to brown nose someone (and maybe you are), when really, you’re just wearing a secret costume on a national holiday.

This costume is one that requires a bit more effort in the planning department. But one exhausting trip to your local thrift store and you’re all set.

What You’ll Need:

  • Class
  • For men, a vintage business suit
  • For women, a vintage dress, pants suit, skirt suit, or maxi dress
  • For men, gel for a slicked back hairstyle
  • For women, pin curls for a big, bouffant hairdo
  • A pack of cigarettes
  • An unmarked glass bottle of scotch or bourbon
  • A checkbook and a pen
  • A misunderstanding of political correctness

If you like how well you are received in this costume, you’re going to have to keep up the charade for months to come. Giving your coworkers and higher-ups such a small taste of what you’re capable of in the fashion department is not only unfair, it’s also illegal.

But don’t worry. Just because Mad Men ended doesn’t mean your job will, too.

5. Your Boss


You may be surprised to know that bosses tend to like themselves quite a bit. So it only makes sense that showing up to work discreetly dressed as them will only end up in your favor. What better way to flatter someone than through their subconscious mind?

What You’ll Need:

  • An outfit in the style your boss or manager tends to dress in
  • A replica of their personality, for fun purposes
  • Probably two cellphones and a bluetooth device
  • Eventually, a headache

If your boss or manager is of a different gender, make it work! It’s 2015. Be a man and wear a skirt if you have to. Women, there are plenty of ways to make it appear as though you have a soul patch. If your coworkers start to ask questions, just stay in character and close the door in their face. If, of course, that is something your boss would do…

6. A TED Talker


If you don’t know what a TED Talk is, then get with it already. If you work in the real world and have seen a TED Talk (or 20…) then you know that it’s all about spreading an idea. So all you have to do is take the idea (AKA what you do at your job) and spread it around the world (aka your office).

What You’ll Need:

  • A headset (it doesn’t matter if it works)
  • If you’re a woman, dress conservatively.
  • If you’re a man, we’re back to the turtlenecks again!
  • A confident walk and/or stance
  • A loud voice
  • Zero eye contact

If you don’t have a headset, borrow (or kindly steal) one from the sales department. If your coworkers pretend that they’re annoyed with all your talking, slowly walk to another part of the office, never breaking your focus.

7. A Member of IT


Who doesn’t love the IT Department!? It’s a world of workers that always have cool snacks, fun novelty sayings on their shirts, and hundreds of complicated memes printed out and taped to their walls for you to read and enjoy while visiting.

From the evidence we’ve gathered in our own office and watching online television, there are basically two types of IT workers: the scruffy, ragamuffin or the straight-laced, fast-talker.

What You’ll Need for the Ragamuffin IT Worker:

  • A novelty t-shirt with an insanely clever, bitter, or super current message regarding technology, media, or both
  • Baggy jeans with pockets full of odds and ends
  • Sneakers, lazily tied
  • A deadpan look in your eyes (when folks from the business side approach)

What You’ll Need for the Straight-Laced IT Worker:

  • A button up patterned shirt – plaid is usually preferred
  • Suspenders
  • Slacks that show off your socks
  • Sneakers that you’ve shined
  • Not cool eyeglasses
  • A very quiet though pensive disposition. Because you’re thinking of everyone’s demise…

Either one of these costumes will probably get you closer to the real IT department and cause you to make new friends or tighten alliances. Which will come in handy when your company computer is on the fritz or you need to ask a secret favor that no one else can know about. Because if there’s one wonderful thing about the IT department, it’s that THEY DON’T DO GOSSIP.

8. A College Professor


You know exactly what we mean here. Someone who’s intellectual, full of wisdom, and is greatly respected by a world of pupils and colleagues. Who wouldn’t want to be THAT for Halloween? Or forever?

What You’ll Need:

  •  A jacket or blazer of some kind. (Corduroy with elbow patches is our personal favorite.)
  • A leather briefcase that’s been put through the ringer
  • The lingering aroma of bourbon and tobacco
  • A constant need to clear your throat, scratch your chin, and wink at those much younger than you
  • A composition book. For when you have time to do a big think.

If this costume reminds you too much of a long lost uncle or an autumn in Maine, then our job here is done.

9. An Investor


If you work at a startup or any sort of company that has relied on the help of investors, this one should be your go-to. Isn’t it fun to pretend you have the world in the palm of your hand? And businesses in the pocket of your billfold?

What You’ll Need:

  • A wad of cash (tucked neatly in a wallet that can fit it)
  • Suspenders
  • A slick comb over
  • A shiny new suit (or one made of a shiny material)
  • A smug grin
  • The walk of someone that knows nothing could ever harm them, monetarily

Feel free to strut around the office. With this costume, you can do whatever you want. Point and laugh at your coworkers or puff on a cigar all day. As long as you stay in character, it’s your choice.

10. A Workaholic


We’re not talking about the television show here, readers. This is the costume of a true, honest-to-goodness employee that has yet to take a sick day, juggles a million tasks at once, works on their lunch break, and is noticeably losing their mind because of it. When a manic workaholic enters the room, it’s hard to look away. For wherever they go, they tend to have a dust ball at their feet and a rain cloud overhead.

What You’ll Need:

  • Bags under your eyes
  • A frazzled hairdo
  • Slouched posture
  • Shirt half un-tucked
  • A high-pitched and very fast way of talking
  • To say yes to every single project someone asks you to take on
  • To cry under your desk a few times throughout the day

Who knows! You may even get a raise because of this one! The worse that could happen is you’ll get more work assignments than you can handle. But the silver lining could be that you’ll finally get your own assistant to help!

11. Someone With the Flu


Despite popular belief, you don’t have to actually have an illness in order to pretend to be someone who does. We all went to middle school. Faking an illness is as simple as hiding your face in a frown.

If you’re trying to get on the company’s good side, you want to go with any other costume in the list above. Having the flu gets you pity, not bonuses.

What You’ll Need:

  • A lethargic expression
  • Unwashed hair
  • A desktop of crumpled up tissues
  • An economy-sized bottle of Pepto Bismol
  • The slowest shuffle on earth
  • A complete lack of joy and engagement in anything anyone says or does, including yourself

If you’re convincing enough, you’ll get to leave early, dress in your dream costume, and hit all the parties before they even start! Because, let’s face it. That’s why you chose this costume in the first place. We know, sometimes it’s boring acting like a normal person all day. And if you can’t celebrate Halloween in the workplace then you might as well take your business someplace else and escape.

That’s what Halloween would have wanted you to do…


Originally posted on Office Pains during the appropriate time of year.


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