17 Gift Ideas For Your Boss Who Has An Awesome Sense Of Humor

by Brittany Bennett
Originally Published: 
Shot of a beautiful young woman using her laptop and credit card while relaxing on a sofa at home
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With the office holiday party plans already in motion, you might be starting to think about little somethings you can offer your cubicle buddies, water cooler work acquaintances, and ... your boss. Whether you're besties with your manager or a little intimidated, it's never a bad idea to get a funny gift for your boss. Think of it as a way to break the ice if you haven't already!

A workplace can sometimes be a stressful environment. Deadlines loom and meetings can be the kind constant public speaking gigs you're not too keen on. This time of year allows co-workers to decompress through the process of holiday office games like White Elephant and straightforward gift exchanges. Break room talk turns into how you're turning screen savers into real life vacation days. A few cubicles might even get dressed up in lights. There's an overall positive, warm vibe jingling through the office. Get your boss in on the giggles.

Your boss, whether they buy happy hour rounds for the company or not, deserves the same appreciation you show your cubicle buddy who helps get you through the day with that constant stream of meme exchanges. I mean, you do have a job after all. And a gift for your boss doesn't have to be a lavish offering, like an already paid for dinner for two at TGI Friday's. It can just be something that makes them laugh. They probably need it more than you know with end of the year deadlines to meet anyways. Get your boss in on the cheer with funny gifts that definitely won't get you fired.

Progressive Expression Socks

Progressive Expression Socks, $10, ModCloth

If your boss sports loafers, they'll need some stylish socks to flash. It's not that progression is funny, per se. It's just not your average argyle sock design typically paired with loafers. You're not just giving your boss socks, you're giving the office a sight to smile at.

Shattered Glass Ceiling Paperweight

Shattered Glass Ceiling Paper Weight, $48, Uncommon Goods

Funny in that oh-so-clever way. And really helps to hold all those paper piling up on your boss's desk for approval. Appreciation and a giggle all at once.

Who Run The Office? Desk Plaque

Who Run The Office? Desk Plaque, $30, ModCloth

You can have a desk plaque facing your office guests and you can have one facing you. You know, to help remind your boss who the boss is.

Adult Award Ribbons

Adult Award Ribbons, $28, Uncommon Goods

Give your boss some credit. You might think the grass is greener, but it's just as much as an achievement to have put on pants and commuted to work for your boss. Give them some real-life achievement awards to hang proudly next to their Ph.D.

Louise Bourgeois Card Case

Louise Bourgeois Card Case, $20, MoMa Design Store

A business card case that's more of a conversation piece.

Adam J. Kurtz "You Tried" Trophy

Adam J. Kurtz "You Tried" Trophy, $10, Fishs Eddy

Sometimes the office environment can be stressful. Lighten the mood with a trophy celebrating some deals that fell through and the effort always put in.

Donut Warming Mug

Donut Warming Mug, $15, Uncommon Goods

Does your boss always do that thing where they have a mug in one hand and something to snack on in the other? This mug is a balancing act that frees up your boss's hand for other business related matters, like signing off on checks.

Small Customizable Light Box

Small Customizable Light Box, $25, MoMA Design Store

Is your boss's role model Michael Scott from The Office? If so, he or she might have endless amounts of fun coming up with creative phrases to light up for the entire office to read.

Toilet Golf Potty Putter

Toilet Golf Putty Potter, $10, Bed, Bath and Beyond

Your boss might be taking more "meetings" in the future once they receive this gift that takes bathroom breaks to the golf course.

Cat Butt Push Pins

Cat Butt Push Pins, $15, Kikkerland

It doesn't matter if your boss is a cat person or not. They're going to be pinning important documents to the conference room board with butts. We might all be adults here, but come on, who doesn't snicker at cat butts?

The Customer Is Always Wrong Mug

The Customer Is Always Wrong Mug, $18, Fishs Eddy

Sure, yes, the customer is always right. But you've complained and you've heard your boss complain about clients or customers. Let them know you're "in" on this joke with a mug that says it all.

Bad Idea/Good Idea Shot Glasses

Bad Idea/Good Idea Shot Glasses, $20, Uncommon Goods

Drinking with your boss? It happens. If you have, these shot glasses could win you a hefty laugh at the gift exchange.

Maki Tacks Sushi Pushpins

Maki Tacks Sushi Pushpins, $9, Perpetual Kid

There is a lot of pinning in offices. Boards are basically wallpaper. If your boss is constantly taking meetings with co-workers over sushi, bring their love for raw fish back to the office with these push pins.

Everything Is Fine Paper Pad

Everything is Fine Paper Pad, $6, Amazon

Sometimes your boss needs a reminder and a laugh.

Top 8 Essential Oils & Oil Diffuser Set

Top 8 Essential Oils & Oil Diffuser, $37, Art Naturals

Thoughtful much? You can take the time to observe that, laugh-out-loud, the office has been crazy busy. With that recognition comes great gratitude for the gift of making your boss's office smell like a spa. Your boss might laugh at how much they needed this.

Mini Office Foot Rest

Geekfactory Mini Office Foot Rest, $12, Amazon

Let your boss know it's okay for her to kick off her heels and do work with her feet up.

E-Cards Desk Calendar

At-A-Glance Year In A Box SomeECards Desk Calendar, $10, Office Supply

This witticisms have been making the internet laugh way before memes and aggravated joke Instagram accounts. As the months go on, have your boss start each 9-5 day with a giggle.

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