Pessimism Expert T-Shirts

Looking for a witty t-shirt for a lover of skepticism? Our tees tap into their dry humor, making a bold statement with every wear.

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"Everything in your life has gone smoothly. That's a violation of Murphy's law."

"Everything in your life has gone smoothly. That's a violation of Murphy's law." mockup

"Everything in your life has gone smoothly. That's a violation of Murphy's law."

from $19.00

Forlornaments: Tools to drain individual and team spirit

Forlornaments: Tools to drain individual and team spirit mockup

Forlornaments: Tools to drain individual and team spirit

from $19.00

Arthur Schopenhauer

from $19.00

"Son, the world is full of disappointments. About 7.7 billion of them."

"Son, the world is full of disappointments. About 7.7 billion of them." mockup

"Son, the world is full of disappointments. About 7.7 billion of them."

from $19.00

Pessimists v Optimists.

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The glass is half full. - '' - 'The glass is half empty' - '' - 'Gah!! No clean glasses!!' - '' -

The glass is half full. - '' - 'The glass is half empty' - '' - 'Gah!! No clean glasses!!' - '' - mockup

The glass is half full. - '' - 'The glass is half empty' - '' - 'Gah!! No clean glasses!!' - '' -

from $19.00

"Today, in all aspects of life losses outnumbered gains."

"Today, in all aspects of life losses outnumbered gains." mockup

"Today, in all aspects of life losses outnumbered gains."

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"A pessimist thinks that we've already arrived."

"A pessimist thinks that we've already arrived." mockup

"A pessimist thinks that we've already arrived."

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'Satchel, life is like a can of tuna...'

'Satchel, life is like a can of tuna...' mockup

'Satchel, life is like a can of tuna...'

from $19.00

"Half Empty. Half Empty. Half Empty-" mockup

"Half Empty. Half Empty. Half Empty-"

from $19.00

'There, Mr Optimist. Now how full is it?'

'There, Mr Optimist. Now how full is it?' mockup

'There, Mr Optimist. Now how full is it?'

from $19.00

Doom & Gloom

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Tom's last day.

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'I make certain all my clients are pessimists...they don't expect to win.'

'I make certain all my clients are pessimists...they don't expect to win.' mockup

'I make certain all my clients are pessimists...they don't expect to win.'

from $19.00

"If, indeed, there is a reason for all this, than that's so much worse."

"If, indeed, there is a reason for all this, than that's so much worse." mockup

"If, indeed, there is a reason for all this, than that's so much worse."

from $19.00

"Look on the dark side."

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"I see fleeting moments of happiness in between extended periods of boredom and stress."

"I see fleeting moments of happiness in between extended periods of boredom and stress." mockup

"I see fleeting moments of happiness in between extended periods of boredom and stress."

from $19.00

The End is Near art gallery opening. mockup

The End is Near art gallery opening.

from $19.00

"Are we pessimists and our stomachs are half empty or optimists and our stomachs are half full?"

"Are we pessimists and our stomachs are half empty or optimists and our stomachs are half full?" mockup

"Are we pessimists and our stomachs are half empty or optimists and our stomachs are half full?"

from $19.00

"Road construction used to bother me. But compared to all the craziness going on in the world, I'll take this any day."

"Road construction used to bother me. But compared to all the craziness going on in the world, I'll take this any day." mockup

"Road construction used to bother me. But compared to all the craziness going on in the world, I'll take this any day."

from $19.00

"Die alone"

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'Barnhill from Marketing will present our economic projections.'

'Barnhill from Marketing will present our economic projections.' mockup

'Barnhill from Marketing will present our economic projections.'

from $19.00

"Maybe you should be depressed, your life isn't that great."

"Maybe you should be depressed, your life isn't that great." mockup

"Maybe you should be depressed, your life isn't that great."

from $19.00

"Oh well - same shit, different day. . .!"

"Oh well - same shit, different day. . .!" mockup

"Oh well - same shit, different day. . .!"

from $19.00

"A glimmer of hope is fine, Hendricks, but anything more than that will lead to massive disappointment."

"A glimmer of hope is fine, Hendricks, but anything more than that will lead to massive disappointment." mockup

"A glimmer of hope is fine, Hendricks, but anything more than that will lead to massive disappointment."

from $19.00

'Some see the glass as half empty, some see it as half full -- I see it as taxable!'

'Some see the glass as half empty, some see it as half full -- I see it as taxable!' mockup

'Some see the glass as half empty, some see it as half full -- I see it as taxable!'

from $19.00

Lent is a real drag this year. - 'Why? What did you give up?' - 'Hope.' - 'I gave up chocolate. Guess what?1' - 'What?' - 'I've made my ideal weight! Yay!'

Lent is a real drag this year. - 'Why? What did you give up?' - 'Hope.' - 'I gave up chocolate. Guess what?1' - 'What?' - 'I've made my ideal weight! Yay!' mockup

Lent is a real drag this year. - 'Why? What did you give up?' - 'Hope.' - 'I gave up chocolate. Guess what?1' - 'What?' - 'I've made my ideal weight! Yay!'

from $19.00

'I feel better today too, but around here I've learned not to be too optimistic.'

'I feel better today too, but around here I've learned not to be too optimistic.' mockup

'I feel better today too, but around here I've learned not to be too optimistic.'

from $19.00

Half Empty/Half Full/I'm Still On Vacation!!!

Half Empty/Half Full/I'm Still On Vacation!!! mockup

Half Empty/Half Full/I'm Still On Vacation!!!

from $19.00

"What? You were expecting good news? Expectations are so-o-o-o passe."

"What? You were expecting good news? Expectations are so-o-o-o passe." mockup

"What? You were expecting good news? Expectations are so-o-o-o passe."

from $19.00

'Would you say this glass is half empty or half full?'

'Would you say this glass is half empty or half full?' mockup

'Would you say this glass is half empty or half full?'

from $19.00

'Taking guard' 'The pessimist'

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'Have you seen the financial pages?' - 'Yes, things are going to get a lot worse before the get worse.'

'Have you seen the financial pages?' - 'Yes, things are going to get a lot worse before the get worse.' mockup

'Have you seen the financial pages?' - 'Yes, things are going to get a lot worse before the get worse.'

from $19.00

Pessimism Expert T-Shirts Collection

Pessimism Expert Mugs

Discover our full collection of mugs featuring clever pessimism-themed designs and witty sayings to brighten their day.

Pessimism Expert Pillows

Check out our humorous pillows that add a dry, witty touch to any room and celebrate their love for skepticism.

Pessimism Expert Prints

Browse our collection of humorous prints to decorate a space with a sharp, cynical sense of humor.