Silly Supervisor Gifts

Searching for a playful gift for a silly supervisor? Our collection features funny and lighthearted items perfect for the boss who never misses a chance to bring humor to the workplace. Whether it’s a quirky mug, a hilarious t-shirt, or a witty print, find something that matches their creative, carefree spirit—ideal for boosting morale and spreading smiles.

All Products Prints T-Shirts Mugs Pillows

Our founder: Custard pies Ltd.

from $19.00

"So what kind of mood is he in?"

from $19.00

'Surely you wouldn't want me to laugh at your joke if I didn't think it was funny!'

'Surely you wouldn't want me to laugh at your joke if I didn't think it was funny!' mockup

'Surely you wouldn't want me to laugh at your joke if I didn't think it was funny!'

from $19.00

'What sort of mission statement is that?'

'What sort of mission statement is that?' mockup

'What sort of mission statement is that?'

from $19.00

'It's a chart of office morale. This is where you went on vacation.'

'It's a chart of office morale. This is where you went on vacation.' mockup

'It's a chart of office morale. This is where you went on vacation.'

from $19.00

'I'll be late for dinner, dear. I'm up to my neck in paperwork.'

'I'll be late for dinner, dear. I'm up to my neck in paperwork.' mockup

'I'll be late for dinner, dear. I'm up to my neck in paperwork.'

from $19.00

"I don't want a G.O.A.T, I want a S.C.A.P.E.G.O.A.T."

"I don't want a G.O.A.T, I want a S.C.A.P.E.G.O.A.T." mockup

"I don't want a G.O.A.T, I want a S.C.A.P.E.G.O.A.T."

from $19.00

Others will fight for you

from $19.00

In/Out/These Things Happen.

from $19.00

'Yes, I know there's a deadline on this project.'

'Yes, I know there's a deadline on this project.' mockup

'Yes, I know there's a deadline on this project.'

from $19.00

Businessman on stilts: 'I had to step over a lot of people to get where I am today.'

Businessman on stilts: 'I had to step over a lot of people to get where I am today.' mockup

Businessman on stilts: 'I had to step over a lot of people to get where I am today.'

from $19.00

'Your resume is a little thin, but I like your willingness to be manipulated by upper management.'

'Your resume is a little thin, but I like your willingness to be manipulated by upper management.' mockup

'Your resume is a little thin, but I like your willingness to be manipulated by upper management.'

from $19.00

'I hate leaving work when I feel I could have delegated more.'

'I hate leaving work when I feel I could have delegated more.' mockup

'I hate leaving work when I feel I could have delegated more.'

from $19.00

'Don't think of it as being a yes man, think of it as being an employed man.'

'Don't think of it as being a yes man, think of it as being an employed man.' mockup

'Don't think of it as being a yes man, think of it as being an employed man.'

from $19.00

"I believe we've found the weakest link."

"I believe we've found the weakest link." mockup

"I believe we've found the weakest link."

from $19.00

"It's a memo from the legal department reminding us to (heh-heh), 'keep our noses clean'."

"It's a memo from the legal department reminding us to (heh-heh), 'keep our noses clean'." mockup

"It's a memo from the legal department reminding us to (heh-heh), 'keep our noses clean'."

from $19.00

Boss's Desk Says No!

from $19.00

'No, your guess isn't as good as mine.' mockup

'No, your guess isn't as good as mine.'

from $19.00

"Don't flutter your little wings on company time."

"Don't flutter your little wings on company time." mockup

"Don't flutter your little wings on company time."

from $19.00

'Let me worry about the one percent inspiration, you just take care of the 99 percent perspiration.'

'Let me worry about the one percent inspiration, you just take care of the 99 percent perspiration.' mockup

'Let me worry about the one percent inspiration, you just take care of the 99 percent perspiration.'

from $19.00

"I'm going to need a little more for the root cause than, who'da thunk."

"I'm going to need a little more for the root cause than, who'da thunk." mockup

"I'm going to need a little more for the root cause than, who'da thunk."

from $19.00

I'm going to practice on you before I start managing other people.

I'm going to practice on you before I start managing other people. mockup

I'm going to practice on you before I start managing other people.

from $19.00

"He's not really much of a leader...he just has a lot of followers."

"He's not really much of a leader...he just has a lot of followers." mockup

"He's not really much of a leader...he just has a lot of followers."

from $19.00

'A few more years in this job and you'll learn how to delegate stress.'

'A few more years in this job and you'll learn how to delegate stress.' mockup

'A few more years in this job and you'll learn how to delegate stress.'

from $19.00

At first I thought it was just coincidence, but then I realized it corresponded directly to your shift.

At first I thought it was just coincidence, but then I realized it corresponded directly to your shift. mockup

At first I thought it was just coincidence, but then I realized it corresponded directly to your shift.

from $19.00

Working hours.

from $19.00

"Well the good news is that after the reorganisation you'll be leading the team."

"Well the good news is that after the reorganisation you'll be leading the team." mockup

"Well the good news is that after the reorganisation you'll be leading the team."

from $19.00

A disgruntled employee chain-sawes hois boss's desk in two.Boss says:'Alright Smith, I'll stop referring to the employees as 'oopsy daisies'.'

A disgruntled employee chain-sawes hois boss's desk in two.Boss says:'Alright Smith, I'll stop referring to the employees as 'oopsy daisies'.' mockup

A disgruntled employee chain-sawes hois boss's desk in two.Boss says:'Alright Smith, I'll stop referring to the employees as 'oopsy daisies'.'

from $19.00

'I'm sorry, but everyone is in a meeting.'

'I'm sorry, but everyone is in a meeting.' mockup

'I'm sorry, but everyone is in a meeting.'

from $19.00

"Remember...when the going gets tough...DELEGATE!"

"Remember...when the going gets tough...DELEGATE!" mockup

"Remember...when the going gets tough...DELEGATE!"

from $19.00

'If corporate lawyers are a dime a dozen, where are the other ten?'

'If corporate lawyers are a dime a dozen, where are the other ten?' mockup

'If corporate lawyers are a dime a dozen, where are the other ten?'

from $19.00

"These are the principal qualities we're looking for in our new recruits."

"These are the principal qualities we're looking for in our new recruits." mockup

"These are the principal qualities we're looking for in our new recruits."

from $19.00

'Bad news, sir -- there's a leak in our think tank!'

'Bad news, sir -- there's a leak in our think tank!' mockup

'Bad news, sir -- there's a leak in our think tank!'

from $19.00

"It has come to my attention that some work-from-home employees aren't maintaining company standards."

"It has come to my attention that some work-from-home employees aren't maintaining company standards." mockup

"It has come to my attention that some work-from-home employees aren't maintaining company standards."

from $19.00

Silly Supervisor Gifts Collection

Silly Supervisor Mugs

Explore more humorous mugs perfect for silly supervisors and add a splash of fun to their daily routine.

Silly Supervisor Pillows

Browse our collection of quirky pillows that bring humor and comfort to any space.

Silly Supervisor Prints

Check out our amusing prints to celebrate the creative, fun spirit of your silly supervisor.

Silly Supervisor T-Shirts

Find more witty t-shirts designed for the playful supervisor who loves to stand out.