Office-Friendly Halloween Costumes for The Modern Man

Last week I got the email:

“We’re going to all dress up for Halloween, here in the office.”

Now, I’m not a total kill-joy in life. I’ve dressed in more costumes than I remember thanks to my years and years in community theater. I’m happy to dress with my kids while we go trick-or-treating.

There’s just something about sitting around in the office, in costume, all day that I don’t get excited for.

Maybe it’s cause I’m older? When I worked corporate jobs, in my twenties, we’d make a HUGE thing out of Halloween. We’d decorate our cubicles, have themed costumes and then all go out for drinks afterwards.

At 43… yeah, I just want to get to go home early and take the kids trick or treating.

This is our office – our place of business. What to do? Forget the Star Wars outfits (they’ll just make fun of you). No Dracula – NO CAPES! If you can pull off a super hero physique in tights – more power to you.

But, for the most part, we just want to wear our own clothes.

I’m not going to be ‘that guy’ who doesn’t dress up. So, how do I thread that thin line of not wanting to dress up, not be a kill joy, and yet still be comfortable at work?

Here are some ideas I came up with…

1. Three-Hole Jim

Jim Halpert never wanted to dress up. He is the champion of “I barely tried”. So… why not go as three-holed (insert your name)?

I’m three hole punch version of Jim. Because you can have me either way: plain white Jim, or three whole punch.

A white shirt with three dots out of construction paper? Yeah, we can handle that.

2. The Cowboy

Jeans, a checked shirt, boots of some kind and a cowboy hat.

I know you have jeans. If you’re a Modern Man (in our 40s), my guess is you have a checked shirt. Right? Yeah, I thought so. Now, if you went through a Country Music Station phase, like most of us did during the Toby Keith era, you probably have a cowboy hat of SOME kind laying around.

If not? Go with the bandana around your neck and you’re still golden. If you’re really into it – do the hat AND bandana. If you’re going for the gold – add some work gloves.

Leave the holster and toy guns at home. Cool to feel like the cast of Tombstone for a little while, but then you’re just a 40 year old guy sitting at your desk with cap guns on your hip.

3. Marty McFly

If you live in the NorthEast – you have a puffy down vest. Then all you need to become our Back to the Future hero is a patterned shirt, jeans, a denim jacket (back in style folks – just ask GQ!) and some Nikes.

If you want to add headphones or lean a skateboard up against your desk, go for it.

Pop culture references can never go wrong.

4. The Construction Worker

Remember that checkered shirt, boots and pair of jeans from the cowboy? Bring them back.

Hit the garage. Add a safety vest you got for bike riding at night, hard hat you use with your chainsaw and some work gloves. Avoid the tool belt – it’s going to catch on your desk chair EVERY time you get up to go to the printer.

If you use your kids’ helmet and tools – you’re definitely going to look like Bob the Builder. As with the cowboy, you could get too close to a Village People character too, so beware how many buttons you leave open on the shirt. In fact, wear a t-shirt under it. You’ll be OK. UNLESS you’re looking for the Village People look – then, by all means – go for it!

5. The Baseball/Football Player on Vacation

Baseball season is now over (congrats Sox fans!). Football is in the highlight of the season.

Most Modern Man have a jersey of some sort in our closets. But, then it gets tricky with what to wear for pants. Baseball pants look silly (love the high socks look on the field, but in the office?). Football pants, well, my wife calls them tights.

SO… how about an athlete on vacation? Jeans (or shorts), sneakers and the jersey. Have a fake cocktail on your desk (add an umbrella for bonus points), maybe a fun straw hat or fedora to complete the look.

Admit it, it’s pretty much what you wear every Sunday, anyway. Right?

6. The Doctor

Have a friend who is a doctor, nurse, PT? Borrow a set of scrubs.

If not – hit up the uniform store. They’re actually VERY comfortable.

Sneakers and a stethoscope from your kids’ doctor kit.

Boom. You’re done and cozy. Plus, people may say “What’s up Doc” to you all day. Bonus!

If you have a beard and need any ideas – check out this awesome post from!

These are just a few of my ideas – what about you? What are you going to dress as? Hit the comments and share so the rest of us can have ANY kind of idea what we’ll be this year.

As for me – what’s it going to be? Check our Instagram Page on Halloween and I’ll share it with ya.


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